First off I'd like to say THANKS to everyone who responded, I got more answers than I expected to get and that's great!
Brian: You really got me thinking with this. A sidekick seems great as you put it, and the waiting thing well that sounds like a reasonable thing too, if they really are coming out with a 3G series. Plus Motorola has never done me wrong in the past. You made it move to the top of my list!
sarahtowny: I've only had one Nokia phone in the past and I had no complaints except the plainess of it. (Of course this was way back when phones were only meant for phone calls and text messaging!) I'll check some of the newer versions out.
detn8r: A Blackberry did come into mind and my main concern was the issue I brought up about people telling me it freezes up oftenly, which you informed me you haven't run into that issue. Also if you tell me to stay away from the old T-Mobile versions of it, I shall listen.
Jeff: I've never had a Samsung phone before, so I'll read more into those. But thanks for the Yahoo! Go link, definately something I'd want on a phone, considering I do use Yahoo! on my mobile a lot.
patndoris: I can definately agree about the AT&T thing which is the main reason I've always been with T-Mobile. Yeah, AT&T does have the whole roll over thing, but for me it was always, "What's the point of roll over minutes, if you have so little minutes and use them all up so have none to really roll over!" (But that doesn't apply to everyone.) Although if I did have AT&T I'd definately go for an iPhone, something about touch screen just makes it so great to me. lol
Once again thanks for the great answers, I'mma keep looking into these phones now with new information in mind and hopefully come to a conclusion soon! Will definately update you guys if I make a choice.