Once upon a time, you'd recommend that people first determine what kind of software they needed to achieve their goals, and then recommend a computer based on the software needs they have. Graphic artists were often steered towards Mac's for this reason, especially in the early days of things like PageMaker. Business number crunchers were steered towards PC's for access to Lotus and WordPerfect. Time moved on of course, but this was always good advice to use when selecting computing platforms.
Smartphone customers could benefit from this as well.
First, make your carrier choice. What do you need? Where will you be primarily using your phone? Are all your friends and family on Sprint? If so, you'll need to adjust your plan to compensate for non-included mobile to mobile minutes. Then compare plan rates which, although very similar, start to differ measurably when you throw in data plans and monthly caps for same.
Second, since we are talking a smartphone, now make your software choices. This to me is the ONLY reason you are buying a smartphone versus a clamshell/flip phone. How easy can you synch the thing to your existing contacts/calendar/email? How easy is it to keep it in synch after the initial setup? What kinds of apps do you want....eReaders, GPS/Mapping, photography/video? Gaming is now huge on smartphones and we are way, way beyond Tetris using the 2, 4, 6 and 8 keys.
Once you've answered those two questions, then and only then should you start focusing in on hardware choices. Otherwise, you are allowing yourself to be totally manipulated by the marketing hype by the respective carrier and/or handset providers. That's fine if you are a sheeple. But a smart consumer makes their own choice instead of letting it be made for them. Specs and horsepower mean very little on a Smartphone as you aren't doing any rendering or DVD ripping on them. What matters is UI responsiveness, battery life, sound quality and screen/visual appeal. Snapdragon this versus proprietary chip X means absolutely nothing if the phone is dead because the battery only lasts half a day. It means even less if there is no software app to exploit that "super duper" CPU.
Personally, I think almost any carrier is fine. They are a commodity in my eyes. And I suspect in their own eyes as well or they wouldn't be selling their service on 1 and 2 year contracts....they know people are promiscuous when it comes to service providers. Depending on where you live and where you travel, some are better than others. AT&T and Tmobile are likely the best choices for someone who travels internationally a lot but lives and works here in the USA. Verizon is a great choice for domestic travelers since their network really does work out in the middle of freaking nowhere (as I can attest while standing in Wall, South Dakota with no service on an AT&T iPhone but 5 bars on a Verizon Droid). From what research I've done, Sprint is likely a great compromise between the coverage of Verizon without the nasty enforced data caps. They all have tradeoffs but honestly having used all of them over the past 5-7 years I can't tell you one is any better than the other. Verizon still has that pesky "can't talk and use data at same time" problem, but thats not as big of an issue as some make it out to be.
When it comes to software, however.....there is absolutely no comparison to the iTunes experience. Synchronization is stupid-simple as long as you've already consolidated your media into iTunes....just plug it into your Mac or PC and done. I will give high marks to Google's synch process as once its done on the Android you'll never worry about losing your contact info again. And its wireless so no need to hook it up to anything.....unless you want to synch EVERYTHING and then god help you with the number of software apps you'll need and the varying degrees of capabilities of each. And then there's the Bloatware, app permissions issues, borderline-malware and shareware-esque thing called the Android Market. For every 10 useful apps you'll find in Apple's curated iTunes App store, you'll have to dig deep to find ONE that can do ALMOST the same job on the Android Market. And its almost always an obvious half-azzed clone of the superior iPhone app. For Android devices, it is NOT a hardware or OS limitation, but my experience with professional paid/free apps on the Android platform are abysmal. Half of them don't work with your specific hardware/OS configuration (and in many cases, you'll find individual versions of the same app posted multiple times for different combo's...making it even more confusing!). And those that do just lack the polish and production values of their iPhone contemporaries. Sure the iTunes App Store has its share of crapware fart apps, but even those are almost universally of a higher quality and guaranteed to work on your iPhone. When the Android does get high production value (Angry Birds is on both platforms, for example) it almost always has adware shoved into it somewhere (again, see Angry Birds as a prime example). I don't know if that's because the Android marketplace is viewed by publishers as "lesser consumers" than iPhone customers or what but for whatever reason, you will always feel like a second-class citizen with an Android. If your needs are basic, you'll get by just fine. But if your needs are basic...why are you carrying a smartphone in the first place?
For the TLDR audience:
In summary, iPhone and the App Store offers a much fuller "smartphone" experience to the average user than you'll ever get from bleeding-edge Android anything on any carrier. This may change with almost half the Android market now stabilizing on Froyo, but I'm not optimistic about that.
If you like shareware-esque applications and don't mind the vast array of Android device differences...many of them feeling quite half-baked....then Android anything on Any carrier is likely a fine experience for you. If you want higher production values and an overall more predictably polished experience.....iPhone all the way.