Good news - T-mobile is back on my good side. I stopped by another store this evening and spent a good 20 minutes playing with a Wing. When a sales person came over, he asked me if I had any questions. I told him I was mostly just playing - to which he asked if I wanted his opinion.
Did I every! This is what he told me: the Wing is slick, but basically painful (in his opinion) to use as a phone. Windows is simply painful to use. The switch from vertical writing mode to horizontal keyboard is accompanied by a noticeable lag of a few seconds. And, if you do leave the WiFi on, it will eat through your batteries in 4 hours.
I couldn't confirm the battery comment - but the rest of the feedback I had noticed in my 20 minutes of playing.
I so wanted to like the Windows UI. But, at the end of the day, it's a desktop UI crammed into a phone - what a mistake. There do appear to be a few keyboard shortcuts, but not as many as I had hoped for.
The only surprise was that the keyboard was nicer than I thought I was going to be. I could see learning to touch type on that sucker with a minimum of effort.
The clerk's recommendation was this: wait till late September and buy the latest Blackberry due out. It will have a GPS, 2.0 MP camera and a full keyboard.
I'm not in love with the Blackberry UI, but nothing is as bad as the Windows UI. As Shira told me - you'll adapt way easier to the Blackberry over Windows.
Someone, anyone, tell me my synopsis of the Windows Mobile User Experience is all wrong. Tell me that once I learn it I'll be flying all over the UI like I do on my Sidekick.
At the very least, my faith in T-mobile is restored.