Portable handheld radios

This is a topical topic for me. We're in the market for a radio setup that will allow us to talk between the car and truck while traveling and that is small enough that they can be used to communicate while backing into spots. Reading this thread, it seems like GMRS radios are the way to go over PRS because of increased transmit power. Couple of questions:

Any brand suggestions?

I see distance ratings for various radios. Do I really need a 36 mile or do something like the 20 mile radios suffice?

Does everyone really get a license for these things or will simply behaving and not acting like clowns keep me out of trouble?

Thanks.