To answer your question: quite simply, the iPhone is *the best* phone for AT&T...from there, you are going to have various levels of sacrifice, so you can get OK phones, but whatever.
Touch Pro 2 shouldn't have MMS problems...but then again, the Touch Pro shouldn't have had them either...if you get a windows mobile phone, however, you should be fully willing to go to xda-developers.org and tinker around (that is, flash new ROMS, download new programs and patches, if need be). That is really what Windows Mobile phone users should just be *prepared* to do.
Maybe you could go with the Blackberry Bold...but RIM's web browser is nowhere in the same class as the iPhone's mobile Safari. (Then again, except for the Pre's browser and perhaps the Android's browser, no mobile browser is really in the same class as mobile Safari. Opera Mobile comes close, which is why I would say go TP2 over Bold maybe...but still, it's a bit different.)
However, I must reiterate the things that some others have said...going from Sprint to AT&T will be costly. AT&T's plans are simply more expensive (if you want the same value that you had with Sprint, you will be paying more than $70...I came from AT&T and I didn't have any problems with them, but I was paying $70 after a discount through my university for only 200 texts a month...whereas for Sprint, $70 gets me unlimited texts), and on top of that, you are likely to have to pay early termination fees (ETFs). These will be reduced by the percentage of your two-year contract that you have already paid off...
I would SERIOUSLY SERIOUSLY SERIOUSLY yell up and down at Retentions to see if they can do ANYTHING about the wrongful renewal. For example, let you upgrade phones for free. Retentions can do a surprising amount of things to keep customers, let me tell you...
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