CTroxtell,
I'm fairly familiar with the Winston-Salem area, and for the best coverage in that area I would say Alltel is the way to go. You wouldn't have any problems falling back onto 'Extended Network' with Alltel because Alltel is the roaming partner for Verizon in that area. But Verizon generally does not provision their customers to use all data features on a roaming network except with certain phones. Alltel allows their customers to use data on a roaming signal, so you should have data just about everywhere you can get a signal, with the exception of towers in extremely rural areas that have neither EV-DO nor 1x.
(If you do much traveling, do be aware that the Alltel roaming indicator is different from Verizon. It will indicate roaming when you're outside of your home area, even if you're still on an Alltel network. I suspect this is done mainly for people on the Greater Freedom regional plan, but it is something to be aware of so that when you go to ... Charlotte or Johnson City or wherever, and you're phone is blinking indicating roaming, you're still on Alltel and the data will work fine.)
With Alltel, on a Smart Choice Pack plan and phone, the plans appear to suit your needs better and you would get much better coverage, especially outside of the Winston-Salem proper where the land gets more rural in a hurry. I've used Verizon and Alltel in that area and I can say, since Alltel has the better plans and better coverage, they seem like the solid choice.
On a regular phone, however, there is no way to change the WAP settings that I've ever read about. The simplistic explanation is because of the software on regular CDMA phones, as you guessed compared to the actual browser of Smartphones.
As for your phone, I would go with the Moto Q. My forte is not in Smartphones, but I do know that the WM5 software that the Moto Q runs will support the chat programs you mentioned, as well as others. The Alltel Moto Q is a solid phone that's a phone first beyond anything else. It doesn't have the touchscreen but it does get reception better than the Palms.
edit: Also, the Alltel version of the Q isn't near as buggy as other reports you've heard of the Verizon and Sprint Q's. The Verizon and Sprint versions were released much earlier, and Alltel took a lot of heat for getting that phone out so much later than their competitors. But now that it is out, it's the smoothest running Q on the market.