I’ve had what could be called a “smart” phone since around 1999, when I worked for a wireless ISV that wanted to make data available to any device at any time, be it a desktop screen phone, voice-read data calls, PC’s, or to uber-small black and white mobile phone screens… yes, hearing people talk about multiple screens and clouds is not a new concept. Sorta like how Facebook is a glorified BBS from the 80’s.

Anyway, since 1999, I tooled around with HDML, WML, skipped the Handspring phone and the Pocket PC Phone, and eventually fell in love the non-touchscreen Windows Mobile 5 because I hated having to use a stylus… when the v1 iPhone hit, it took me a while to get past using the on-screen keyboard – and having to re-learn how to TXT – but I eventually got there and have stayed through to my current iPhone 4. I’ve been around the block more than a few times with devices and have watched them get better with each generation.

This weekend, I pulled my SIM from my iPhone, put it into a Windows Phone 7 Samsung and spent the entire weekend without an Apple product in my pocket.

The Hardware – not much to add to the reviews of the hardware at this point except that I’m digging the subtile variety of the handsets that are out there, which is something you just don’t get from Apple. The device I used has a great screen, a good form factor, with no slide-out keyboard. Want a slide-out keyboard? Get a Dell or an HTC. One of the HTC models even has slide-out speakers. Any as sexy as the iPhone? Yeah, actually a few are on par, and even lighter since there’s less glass, but for me the big thing is the thinness, the screen, and the software. One thing that is still exposing itself is the memory upgrade story: right now most handsets come with less than 16GB of RAM but some also have microSD slots – that should easily take the handset up to Zune HD levels of 32GB or higher.

Gripes? No one seems to have a physical switch for silent mode and I have no idea what the hell that’s about. I can also see how some of the non-physical buttons can be weird, but not deal breakers.

The Software – this is where things get tricky… there’s the core OS, and what that does, and then the flood of apps that extend the experience of the OS.

The OS. Honestly? I like the UI. I like that the WP7 tiles have real time information on them, much like how the calendar button on the iPhone changes each day. I also like the hubs, particularly around Marketplace, Music/Video, and Games. The People hub could be good, but for me, it had some challenges… as part of my sign up, I gave it my Windows Live ID, because I wanted to see my Avatar within the Xbox LIVE app. That instantly pulled in all of the Contacts I had for that account. The problem is that this was a long list of Messenger contacts (who I don’t call) and my entire friends list from Facebook (which is a ton of people). What I wanted to sync was my collection of Contacts from Outlook on my home PC – which is where I started syncing media from – but this is not supported. To get around this, I put all of my phone Contacts into a different WLID account and sync’d that over; I then disconnected Facebook from my other WLID account because there was no way to exclude these contacts in the People hub. My guess is that this’ll get un-screwed up in future releases. One thing that was very nice about the People hub is that I had the option to bring in all of my Facebook contacts separately and keep them out of the “phone” list… then I was able to Link contacts from all three accounts together. So Jolene’s phone contact linked to the Messenger information and pulled in her Facebook image into the phone list. That is some very slick work.

Gripes? Sure. No custom ringtones, I don’t think. The Map application works pretty well but directions were slightly off on some routes in Seattle. Not horrifically bad, just missed a side street that I could have taken to shorten the route. No Visual Voice mail, which I didn’t think I would miss since I never get any… was more of a “Aw, that’s not here”. Maybe AT&T will release an add on app. Also, I’m perplexed that I can’t sync more information from my PC version of Outlook. The iPhone took most of its PIM content from my PC, but the WP7 sync is looking to the cloud for information syncing… maybe it’s time for that transition, but I didn’t think it would take that many changes… for example, I’m bummed that I can’t keep my Facebook link to the WLID account; chatting in Messenger to people in Facebook was really good stuffs.

The Apps. I expected to have application withdrawal. I planned for it. Waited for it to show up for hours. Didn’t happen. I’ve always said that changing from the iPhone would be a huge pain point because I was so invested in the platform… it’s true that I have spent some money on some apps and some games but I didn’t spent that much… what did I look for and not find? Not much, really. OneBusAway and Seattle Traffic were there. Netflix, YouTube, IMDb, Facebook, Flixster, ICanHasCheezburger, Yelp, and Shazam are all there. What did I miss? Angry Birds, a little bit. Couldn’t find an app that uses barcodes – on the iPhone that’s RedLazer, Target, PriceGrabber, and Amazon. No Kindle software either. Yet. And I mean “yet” because I have to expect that they’re coming. There’s no reason not to. These phones are going to do well enough to get bits from all of the usual players… I did find myself going to the web more than I remember because there weren’t a lot of the store apps I’ve gotten used to having, but that’s not a problem either. I mean do I really need a Best Buy app when they have a web site that’s fine tuned for mobile devices?

Did it beat the iPhone and Android? It depends on your background and how trained you are for the device you currently own. It also depends on how open to new experiences you are and how much time you are willing to dedicate to re-learning things… I still use a PC because it’s the best and easiest tool to get stuff done. Why not a Mac? I’ve tried to convert many times… each time I find myself working harder to do the same tasks that I already know how to do on a PC. I have to unlearn that which I’m used to. For WP7 vs iPhone, that’s the thing here too… I would have to unlearn a lot of good (and bad) habits that I’ve developed using an iPhone all this time. The shortcomings of the iPhone don’t upset me much anymore – and there are many – because I’ve lived with them all for years. WP7 comes with a new set of features that address some of the iPhone’s shortcomings but there are other things that will force me to change behaviors… and I don’t know if I want to do that right now. And Android… the only two things that have interested me in Android since it’s creation were the choice of cariers and the new swipe-selection-keyboard that I saw on a Galaxy S for the first time today. Everything else about Android just makes me go “meh”.

For new users and casual iPhone users, I think that Windows Phone 7 is a no brainer. You have a choice of devices and a choice of hardware that you don’t get from Apple. You could make a case that “WP7 really only works fully with a Windows Live account” meaning that you have to buy into the whole Windows Live ecosystem, but I don’t know how accurate that is, since the things that required WLID do so everywhere else, like Xbox LIVE. Besides, with the iPhone, Apple has very “strong” direction to use their Apple ID system and services. In fact, Apple is far worse to users that want to do something outside of their ecosystem… so that’s a push in the comparison list. One thing that was really nice was when I realized I got a whole suite of tools from http://windowsphone.live.com that Apple charges for, with Mobile Me. To that end, if I had never used an iPhone, I would switch without a moment’s hesitation.

But… I have used an iPhone for almost four years now. I’ve been through many, many iOS upgrades to get the phone to where it is today. I paid my dues when there was no copy/paste, when there were no custom ringtones, when there was no way to group icons together, crappier than not network support, and all sorts of issues… it’s evolved over the years to a pretty comfortable device. WP7’s first release is leaps ahead of iPhone v1 but there are still somethings that are missing that would make it require some extra effort to switch to it. For example, data migration: how do I get my saved games over to a new phone? iPhone to iPhone you can restore a back up, unless you’re told by Apple to rebuild the phone, but from platform the platform? It’s a challenge, but I honestly think that this is the first of many steps for WP7; it’ll only get sweeter from here and they’re starting in a good place.

Odds are I’ll still buy one since it’s the best mobile Xbox LIVE experience I can get; if I can get the memory up to 32GB, the Samsung Focus (with the AMOLED display) can replace my Zune HD… whether or not I swap the SIM for a longer stretch is a question for a later date.