This year I decided to buy an unsubsidized iPhone so I could save a bit of cash on my monthly wireless bill, and so that I could own my iPhone.

But, the more I think about it, the more I wonder if that’s the best route after all.

Over on Lifehacker, Whitson Gordon crunched some numbers comparing the cost of a new phone to the value lost over 1, 2, 3, and 4 years. In short, if you’re holding onto your iPhone for 2-3 years in order to save money on upgrades, it’s actually not that much money saved compared to just buying a new model and selling your old model year over year.

This, of course, assumes that you are selling your old phones when you buy a new one.

However, nowadays, all the wireless carriers are making it much more difficult to buy a subsidized iPhone (which is why I decided to go with unsubsidized).

If you’re able to wrangle your carrier into selling you a subsidized iPhone, or you’re willing to just buy one unsubsidized, then you can rest easy to know that you’re spending about 1/2 as much compared to leasing your iPhone.

But, that’s only if you’re selling your year-old hardware on Craigslist or eBay. Which has become a challenge these days.

And thus, for those of us who don’t like to hassle with selling our iPhones on Craigslist / eBay, we trade it in to Gazelle. But Gazelle doesn’t pay as well (because they have to make a profit as well) and thus your net expense of ownership goes up.

And then there is another thing to consider: with Apple now also offering their iPhone leasing/upgrade program, it makes me wonder if the resale value of an iPhone will go down in the coming years. I suspect a lot of people will prefer to pay $32.41 or more per month and just trade in their previous iPhone in order to upgrade every year.

Here’s another way to think of it: a base-model iPhone 6 costs $649 unsubsidized. If you buy it, keep it in pristine condition, and then sell it one year later, you’ll get as much as $450 on eBay or Craigslist, or as little as $320 on Gazelle.

In that scenario, you’ve spent between $200 – $330 to use your iPhone for a year.

If you were to use that same iPhone for a year, except this time go through the Apple Upgrade plan, it would cost you $389 ($32.41 x 12).

And so, while Apple’s Upgrade Program is $60 more expensive at best, it also comes with Apple Care, and you don’t have to worry about keeping your device in pristine condition in order to get maximum resale value from it at the end of the annual upgrade cycle.

From where I’m sitting, if you like to upgrade every year, if you’re not ultra-thrifty, if you don’t care about keeping your old hardware, and if you like to pay for convenience, then Apple’s Upgrade program actually sounds like a pretty sweet deal.

The live stream aside, this week’s Apple event was great. Now, I know these press events aren’t technically meant to be entertainment — they are mostly meant to be informational — but, Apple has always prided themselves in putting on a good show with these events. As a performance — as a “show” — the WWDC keynote was far more fun I thought. Today’s even was great in its own way.

Tim Cook was in rare form on stage. He had a blast showing off the Fallon / Timberlake commercials; he was super excited to show the Apple Pay demo video — so much so that he showed it twice in a row; he was awkwardly giddy at the end when he and Bono announced the free U2 album on iTunes.

Cook was more relaxed — almost giddy at times — compared to past keynotes. He was wearing his heart on his sleeve more than normal. Not a lot, but it was certainly noticeable.

My hunch is that Cook’s excitement had to do mostly with the Apple Watch.

Perhaps Tim Cook had a deeper hands-on role with the development and vision for this device than any other Apple product. As CEO, all the Apple products are like Tim’s kids. And ask any parent, you can’t pick one kid as being your favorite. But, with the Apple Watch being the first major new product in a new category to ship during his tenure as CEO, perhaps Tim Cook is more sentimental about this product release and announcement than others before it.

That said, here are a few miscellaneous thoughts and observations about the event and the cool new products we’ll all be waiting in line to buy.

The Live Stream Fail

It was an epic failure for the first 25 minutes. All around the world the Apple site was up and down, the live stream was failing, and when it was on, you could hear Chinese overdubs — you could hear both Phil Schiller and a translator talking simultaneously.

At just about 30 minutes into the event, the live stream started working again. But Apple introduced the iPhone so quickly — it was announced within the first 10 minutes of the show — that by the time the live stream was back up, Phil Schiller was almost on to talking about pricing.

The iPhone 6

The days of secrecy are long gone. We had rumor sites with full models of the iPhone 6 — we knew what it would look like. And we knew there would be two sizes: a 4.7-inch and 5.5-inch.

I haven’t had any actual hands-on time with either iPhone, but I did print out a paper mockup of each phone to get an idea of what the dimensions actually look like and how they compare to my current iPhone 5s. Yes, this sounds goofy, but based on the paper mockups I printed out, the 4.7-inch iPhone 6 doesn’t seem unreasonably large.

I am a person who prefers a smaller phone. I also spend far too much time each day using my iPhone, and so I appreciate any and all additional screen real estate that doesn’t come at the cost of physical usability. For me, I want to be able to easily pocket my phone and be able to easily hold it. The 4.7-inch seems to meet all those criteria.

Remember how freaked out we were about a 4-inch iPhone? How “perfect” the 3.5 inch screen was? And how nervous we were about a hypothetical 4-inch phone hindering us from being able to tap on every pixel and easily use the phone with one hand? It took a little getting used to, but everyone I know quickly acclimated to the iPhone 5/s. It is noticeably thinner and lighter than the iPhone 4/s, which helped, and once we got used to the additional screen space, the 3.5-inch screen of the phones of yesteryear felt stubby and cramped.

I suspect that is exactly how it will bode for those of us upgrading to the 4.7-inch iPhone 6. The new iPhone 6 is significantly thinner than the current generation, and with its curved edges will not feel too big. Just like the iPhone 5 compared to the iPhone 4, the iPhone 6 is mostly just taller. Though in this case it’s not only taller. It is also just a little bit wider.

In a month from now, those whom have upgraded will be acclimated, and when they look at the “small” 4-inch screen on the iPhone 5 they will wonder how they ever got any tweeting done in such a crowded pixel space.

The question is, of course, if Apple is going to stop here? How big will the smallest iPhone get? How long will the iPhone lineup consist of 4-, 4.7-, and 5.5-inch phones? Will 5.5 one day become the new smallest size? I hope not, but who knows?

The mobile phone market has asked for bigger phones and Apple has responded. Because not only does Apple want to make the best phone on the planet, they also want to sell as many of them as possible. This strikes me as a pragmatic move on Apple’s part — this time they have skated to where the puck is. Instead of holding their ground that their first design decision was the right decision forever, they are willing to make concessions to serve what the market wants. And the market wants freaking huge phones.

After the keynote was over, I asked on Twitter what size iPhone people were going to get. The replies were split almost right down the middle — a lot of people want the 5.5-inch iPhone. And I think it’s going to prove a huge success. Though it doesn’t appeal to me, those who do get one I bet will rave about it. Sort of like all those folks who got iPad minis when everyone else was holding on to their full-size iPad because “you can’t do real work on an iPad mini.” Well, I bet most of those who buy a 5.5-inch iPhone 6 Plus will never go back.

That Protruding Camera Lens

Kinda ugly right? Kinda “not like Apple,” right? Well, I think this is a place where Apple has shown their hand at just how motivated they are to keep progressing the camera technology in their phones. Their engineering team has made a phone so thin that they physically can’t pack the lens and sensor into it.

Remember with the iPad 3 and how it was slightly thicker and heavier than the iPad 2? It had to be in order to accommodate the bigger battery that was powering the Retina display. Apple had to choose between a device that was as thin and light as its predecessor, or one that had good battery life. They chose battery life.

With the iPhone 6 and 6 Plus, they’ve chosen to make the camera as good as they can make it, even if it causes the lens to slightly protrude. As much as Apple is known for their design and good taste, let it never be said that they will chose form over function when it comes to the most important features.

One More thing…

When Tim Cook announced the Apple Watch (it’s going to take me a while to stop saying “iWatch”) he was grinning ear to ear. As I mentioned above, his excitement and giddiness were palpable.

Cook said how Apple loves to make new products. They love to make technology more personal. This could have been a place to show the slide with the street signs showing where technology and the liberal arts intersect.

Cook said he was excited to announce an entirely new product. That it will redefine what people expect from its category.

He then cued the video that revealed the Apple Watch.

After the reveal, he came back out on stage. His shirt sleeves rolled up with a white Apple Watch Sport on his wrist. And he gave a few fist pumps into the air. The room was cheering and Tim Cook was genuinely excited and happy.

As Cook began to talk about the Watch, he called it the most personal device Apple has ever created. “We set out to create the best watch in the world,” he said. And then he gave the four main bullet points of what makes it so great:

• Precise (keeps time to +/- 50 milliseconds)
• Customizable (sizes, bands, metals)
• New way to connect and communicate directly from your wrist
• Comprehensive health and fitness device

The Watch, of course, does so much more. It can be a remote for your Apple TV, it can show you notifications that are coming in on your phone, you can start reading an email on your watch and then “hand off” that email to your phone to reply, you can use it as a viewfinder for your iPhone’s camera, there’s a Walkie Talkie feature, and more.

But the core functionality of what Apple is shouting from the rooftops is 4-fold: precision, personality, communication, and health. I want to talk briefly about the latter two.

Communicate directly from your wrist

Communication is critical. We want more than just a remote control for our iPhones, we want something that can function like a miniature phone. This has been the promise of all the smart watches that have come before: view incoming notifications, control your phone, save the world. But they’ve been underwhelming because they are difficult to operate and don’t actually make things easier than just pulling our phone out of our pocket.

The Apple watch has some clever features from iOS 8, such as the intuitive reply buttons where it can guess what your reply will be to certain text messages. And there is Siri — you can dictate to your Watch for sending messages. And then there is this other way that the Watch lets you communicate with others (who also have a Watch).

Bring up a contact and you can send them small drawings, morse-code, and even your own heartbeat. There is a purity and childlikeness to this watch-only communication method that I am absolutely intrigued by. As a user, I think it’s clever and beautiful. And from a marketing standpoint, it’s also a brilliant way to encourage people to buy a few watches and give them to their friends. I know that if I buy one, I’ll probably buy two — one for me and one for my wife.

Comprehensive health and fitness device

The health and fitness features will be, I think, the Watch’s “killer app.”

For one, there is a huge market for this. The small wearable device that tracks our movement. Well, the Apple Watch does so much more than just track our movement.

They say that a big part of what separates lifelong athletes from casual exercisers is those willing to do the same workout day after day after day. Well, a big foundation that helps with keeping the motivation to stay healthy and fit is to have tangible short- and long-term goals as well as the encouragement and cheers of your peers.

The Apple Watch seeks to aid these in a new and unique way. Of course, it tracks our activity and movement, but it can also monitor the intensity of our activity. And it sets goals for us, such as to stand for at least one minute every hour. And then it communicates with our iPhone to provide reports and give us reminders about staying active and what our progress is. The data collected by the M8 processor, the pedometer, and the GPS of our phone and watch, combined with the fitness apps, combined with Health Kit, make for an impressive and comprehensive toolset for the average person to be more informed about their personal health.

Not only is that a popular thing right now, but it’s also a good thing. They say people watch an average of 5 hours of TV every day. Many of us work desk jobs and we sit in front of a computer for many hours at a time.

I live in Kansas City, Missouri and we are ranked as one of the most unhealthy states in America. We are also the BBQ capitol of the world, so…

But my point is, many of us are sitting down most of the time and we don’t get outside nor do we go to the gym. And if we did want to begin getting in shape, where do we even start?

While Apple can’t answer that question, they can make some significant innovations that will not only raise people’s awareness of their own health and activity, but it will also, hopefully, give them some tools and motivation to do something about it.

And for those who are already active, now perhaps there is a device that will help them with their goals and also be fun and delightful to use.

The iPhone changed everything. It redefined what “delight” in software means. It pushed the needle of mobile and touch computing far forward. It opened up a massive ecosystem of apps and services and has been a key player in the boon of social networks.

I’ve had an iPhone within arms reach since 2007 — it is one of the most important gadget I own (if not the most important). As the software and hardware have evolved over the years, here’s a look at what apps have settled in as the ones I use every day to get things done and communicate with other people.

Let’s start with the apps I use on a regular basis for work and for play, these are my Mission-Critical Apps

• Simplenote: My thoughts on Simplenote always start along the lines of how it’s the app I’d chose if I had to pick just one app only for use on all my iOS devices. For me, hands down the most important “workflow thing” is to have text in sync between my iPhone, my iPad, and my Mac. There are a lot of apps which do this well, but for my needs, Simplenote is the best.

When it comes to my writing workflow, I’ve basically got two buckets for all my text. First there is my bucket of ideas, lists, thoughts, and all sorts of other miscellany. And second is my bucket of current articles I’m working on. The former is what I use Simplenote for; the latter is a Dropbox folder filled with markdown files.

What makes Simplenote my favorite here is its search functionality. Simplenote has amazing and fast search. Searching for a note searches both the note’s title and the contents within. Then, tapping on a search result from the list takes you the search results within that note where you can the see all instances of that term within the note’s contents.

• Byword: Byword is my next favorite text app on the iPhone, and it’s the app I use for my second aforementioned bucket. For any article I’m currently working on, if I want to edit, add to, or create a new one from my iPhone, then I use Byword to access my “Currently Writing” folder.

Byword has some awesome features that I wish Simplenote did — namely, fantastic Markdown support and a dark theme. Byword’s search functionality is also fantastic — better than any other app I know of, save Simplenote. Byword would make a great app for all my “little notes”, but it doesn’t (yet?) show search results for terms within the note’s content (though it does search a note’s content when searching at the list level).

For more about why Byword is awesome, read our review at The Sweet Setup (written by Federico Viticci) where we crown it the best Markdown Writing App on the iPhone.

• Fantastical: I’ve spent hours and hours testing, trying, and using many different great calendar apps for the iPhone. And Fantastical is the best. Natural language entry for creating new events is the easiest way to go about it, and Fantastical has the best natural language engine. Not to mention Fantastical has several excellent design layouts (day ticker with list view; month view with list view; and landscape mode’s week view) as well as reminders support. The only thing I dislike about Fantastical is that it lacks an iPad version.

• OmniFocus: I’ve been using the OmniFocus suite of apps (Mac, iPhone, and iPad) for over three years now. Once a year, usually around the New Year, I like to step back and consider if the tools I’m using are still the best tools for me. If the answer is “yes” then I leave things alone and get back to work. But if the answer is “no” then I try to consider if its my use of the tools or the tools themselves that are flawed.

Lately, I have been wondering if OmniFocus is now too complex for me now that I’ve somewhat settled into a grove with my work-from-home schedule. But as I’ve considered other alternatives, I just can’t conceive of quitting OmniFocus because it’s a task management system that I trust — I know that if and when an important task becomes due, OmniFocus will show it to me.

This is something that I will be revisiting in the near future but for now, OmniFocus remains one of my “mission critical” apps (on all devices).

• Day One: This is certainly the best journaling app out there. I keep Day One on my iPhone’s Home screen and write in it often. I have no rules for how I use Day One, nor for how often I use it. My entries are all sorts of things, including photos, one-line milestone mentions about my kids, deep thoughts, brain dumps of ideas, and more.

• Tweetbot: My go-to Twitter app, and arguably the best Twitter client on the iPhone. I’m a huge fan of the big update Tweetbot received a while back and look forward to that update influencing the iPad and Mac versions as well.

• 1Password: I sometimes like to refer to my iPhone as “Command Central”. It’s great for a lot of things, and then okay at a lot of other things. And while it may not be the best device for some tasks, I can still do pretty much anything from the iPhone if and when I need to. And since I have my iPhone within arm’s reach pretty much 24/7, it makes sense that I should be able to access critical information when I need to. And that’s why 1Password is so great.

1Password is far more than just a password manager. If that’s all it was then the updates to iCloud keychain sync would have negated the need for 1Password. However, 1Password also stores secure notes, bank information, and pretty much anything else I can think of.

• Rdio: This is the app I use for listening to music on my iPhone, iPad, and Mac. The $10/month plan is well worth it for getting unlimited access to pretty much any album I want.

• Instapaper: It seems everyone is using Pocket these days, but Instapaper continues to be my go-to Read Later app. I love the design and I’ve got an IFTTT recipe that takes all of my Instapaper “liked” articles and drops them into Pinboard for me. Since having kids I now use the iPhone version almost as much as the iPad version. There are often times I’ve got just one hand free and it’s a great time to catch up on some reading.

• Poster: This is the app I use to post links to shawnblanc.net; alas it’s no longer available for sale because the developer, Tom Witkin, now works for WordPress. Fortunately for those who already have Poster, it is still being updated.

• Scratch: If you consider yourself an “iPhone toting power user” in any level at all, then you probably want a quick-capture text app such as Scratch or Drafts. I’ve gravitated towards Scratch on my iPhone mostly because I like the design, but that in no way means Drafts is an inferior app. In fact, Drafts does a lot of awesome things that Scratch does not. I use Drafts on my iPad, and have a cool URL-scheme workflow thing that helps me get links and text from Instapaper to Poster (with Drafts as the mediator).

• TextExpander Touch: Though it’s not really an app that I launch, many of the apps I use support TextExpander snippets.

• Dropbox: This app/service could go without saying, but yet, at the same time, it’s worth mentioning because Dropbox is such a critical back-end component to so many of the apps I use. I use Dropbox to sync my 1Password database between my iPhone, iPad, and Mac. I use it to keep all my “Currently Writing” articles available to me on all my devices. I use it sync Day One, and my TextExpander snippets. Moreover, since all my current projects have folders in Dropbox on my Mac, I can access those files at any time via the Dropbox app on my iPhone.

And now let’s talk briefly about the apps I don’t use all the time, but which I use often enough and are awesome

• Check the Weather: This is my favorite weather app. It’s very easy to read, and I like that it has a radar and Dark Sky’s short-term precipitation forecast.

• Google Maps: It’s just more reliable than Apple’s maps, and it’s far better at finding the place I’m searching for.

• PCalc: PCalc is one fine calculator app. I use it not because I’m an engineer nor am I an amateur calculator nerd, but because it looks great and it’s fast.

• Reeder: My favorite RSS reader, though I mostly use the iPad version.

• VSCO Cam: My go-to app for editing photos I take with my iPhone.

• Riposte: The best iPhone client for App.net.

• Mileage Log: For years I used Trip Cubby to track all my business, medical, and charity-related driving. That app was recently retired and out of the ashes arose Mileage Log. I haven’t used any other mileage tracker so I don’t know how this one compares to the others, but I do know that Mileage Log is awesome and it complies with the IRS’s regulations for tracking miles driven for tax purposes. I’ve used the app to log 62 trips so far this year for more than 1,300 miles.

• QuickShot: I use this to take photos of business-related receipts for tax purposes. QuickShot names them with the date and uploads them to Dropbox. Then I have a Hazel rule that moves those images to my receipts folder and I throw away the physical receipt. It’s faster than scanning them all in at once (especially since receipts are good at getting all wrinkled up in my pocket), and it’s a great way to keep track of receipts when traveling.

• Loom: After Everpix shut down I switched to Loom at Bradley Chamber’s recommendation. There are a lot of things I like about Loom (such as its design and auto uploading of images from my Mac) and it’s still better than Photo Stream when it comes to don’t-make-me-think-about-it photo syncing from all my devices to all my devices.

• Paprika: I’ve recently migrated all my recipes out of Simplenote and into Paprika. I don’t have a lot of recipes, but the ones I do have are so very delicious and it makes a lot more sense to keep them in a nice recipe app. Paprika is truly quite great, and having a 3-app suite across the Mac, iPhone, and iPad has proven to be quite helpful. Over on The Sweet Setup we tested quite a few recipe apps and found Paprika to be the best.

• Checkmark: I don’t use location-based reminders on a regular basis, but when I do then Checkmark is the best there is. It’s fast and reliable.

• Delivery Status: This is a swell app that keeps track of packages and deliveries I’m expecting.

• Dropvox: This app is extremely dated, but it still works and I still use it to record Shawn Today episodes whenever I’m away from my Mac. And, so far as I know, there are no other apps which take a voice recording and pipe it to Dropbox.

• Pinbook / Pushpin / Pinswift / Pinner: There are a lot of good Pinboard apps out there right now. Pinbook was my favorite for a while, but it’s in desperate need of a good update. Pinswift is new and pretty great. Pinner is also nice. The jury is still out on this one, but needless to say, there are quite a few nice options for anyone in want of a good iOS Pinboard client.

* * *

About 9 months ago I began taking monthly screenshots of my iPhone’s Home screen so I could track, over time, how my usage of apps evolved and changed.

This is what my Home screen looked like on March 1, 2013 compared to how it looks today:

As you can see, aside from the visual change iOS 7 has brought, not much has changed for me in terms of my most-used and most-important apps.

I find this awesome and yet also a bit curious. It’s awesome because I feel comfortable with my current arsenal of 3rd-party apps; they do pretty much everything I could ask of them, I know what they’re capable of, how they work, and how to use them efficiently. However, on the other side of the coin, there are some apps I use that don’t have any other top-shelf alternatives which interest me.

Is that a bad thing? No, I don’t think so. Naturally, I want 1Password to stay the undisputed champion of password management apps because not only am I familiar and happy with it but also because I’ve invested a lot of money on it. However, on the other hand, competition breeds innovation. When an app sits as king of the hill, with little to no competition, I can’t help but wonder if it’s the best version it could be or if it’s just the best when compared to everyone else.

But let’s not end on a sad note. To wrap up, let me say that I find my iPhone as interesting, curious, and wonderful today as I did in 2007. My kids will grow up thinking iPhones and iPads are normal, and who knows what this stuff will look like when they’re my age. But I’m glad I’ve had the opportunity to be right here, living and working in the midst of what is undoubtedly one the most significant evolutions of personal computing since the 1980s.

But now I’m crossing into iPad stuff. And that’s a post for next week…