I think you'll be happy with either the Icom 208H or the Yaesu
FT 7900. If there is any way that you go to a shop to play with them both before making your decision, that would be best. If crossband repeat is important to you, it might be worth trying to find a used Yaesu
FT-8800. They are a little more than your budget when purchased new, but I bet you could find a used one that would let you get it in your Jeep.
That Yaesu
FT-10R is a cool little radio also. If you are going to have the top off on your jeep and be in an environment where it could get wet, then that is the radio for you. I played with that one a bit at Dayton, and it is really neat for a rugged / all weather type of environmment!