Donnie,
The smart thing to do would be to find out what bands are in normal use in your area and use that for a base for a radio requirement. Around here, 2 meters is in use, and 70 cm. BUt how about if you go somewhere? If the cost doesn't stop you a dual band radio is very nice to have, gives you some common options. I'm a Kenwood fan so guess which brand I'd recommend! That's a personal preference and will be different for everyone.
How about all the 'bells-n-whistles'? Most of them are usually nice to have, but just how often will you use them? Beats me, no idea which would be useful to you. With some of those 'bells-n-whistles', once you've played with them for a while, they won't seem so 'useful' anymore. And then some of them you'll never quit using. For instance, I think there's one 'D-Star' radio in this area. It isn't mine, and from the 'looks' of it, I don't think I'll ever have to worry about getting one. Same for a 'band-scope', nifty little things but not all that useful for me. The only 'option' that I would definitely recommend is those 'tones', PL, CTCSS, whatever. They are NOT options any more, they are a requirement for repeater use. That tends to rule-out a lot of 'used' radios that otherwise work just fine. Then again, you can add a 'tone' board to almost anything if you want to bad enough, you know?
And then you should think about future up-grades! That's not really a biggy, but keep it in mind. I honestly don't know of many people who never change radios at some point. I doubt if you'll be the exception, sort of.
Have fun.
- 'Doc
(The hardest 'best' solution is to get your hands on, and playing with something before getting it. See how you like it.)