Not a stupid question at all. For what you want, voice and texting (with, I assume, email and some light browsing), I can't see any reason not to go with a "newer" 3G phone (Droid X2, Incredible 2, Droid 3, etc.) that doesn't require flashing. If it turns out you want to do more (which would be ?... I'm not quite sure what) then you could always buy a newer phone and flash it. Right now I'm using a Motorola Admiral on RingPlus and it's a big step up from my XPRT only because it has more memory. That why I suggest something in the newer 3G phones, they started getting more RAM with each release and that's a big help.
Originally Posted by pc.colfax
EDIT: Some mention a big advantage in using Android 4.x -- and maybe there are advantages but I don't know what they are. My wife has Android 4.x on her Note II but -- since I'm used to Android 2.3.x -- I like my version better for what I do. Again, I'm not a huge Internet user, nor do I engage in "social networking" so maybe that would make the difference.
Motorola Droid X2 on Budget Mobile & Motorola Admiral on RingPlus -- both rooted but running stock Android 2.3.5