Good luck with it, I think you'll enjoy it, I have. (The radio part, not the jeep thingy.)
Most ham radios aren't the simplest thingys in the world any more. Usually have lots of menus to figure out, etc (has to do with small sizes of radios). So 'simple' is nice till you get your feet wet, sort of. And since you plan on using this when you're mobile, or moving, that 'simple' can make one @#$$ of a difference.
Nothing wrong with small radios, or handy-talkies, but since then are going to require some attention, sometimes they aren't the best "starter" radio you can have. Handy-talkies are especially not suited for a 'starter', they are very limited because of their antenna, just not a very huge 'range'. With VHF/UHF you are looking as sort of short range to start with, so why limit yourself even more with a handy-talky? Later, after you get your feet wet, and if you want one, have at it!
That "getting your feet wet" thingy is always going to be sort of expensive, sort of. Mainly because that's about the only way to get exposed to various radios and their "style" of doing things. If you can get some eye-ball, or hands-on experience with something before you buy it, it makes things much simpler/cheaper, you know? Good luck with that! Just wish there were a dealer closer than 200 miles from me, would have made things much easier.
I would also suggest NOT stopping with the Technician class of license! It limits you to VHF/UHF primarily, which ain't bad, but there's a huge number of other bands to play with too. It isn't that bad, just do it!
And the important part, have fun.
- 'Doc
"If you ain't got Kenwood, you got squat!"
"I Can Only Monitor, is better than nothing."
and...
"Who would want anyting with 'AES' in the middle of it?"
..... couldn't resist.