I've had 2 different handhelds and 3 mobile radios since getting my license. For what they're worth, here are some thoughts.
A handheld (HT) is nice to have when you're out of the vehicle, but while inside it can be a pain. Transmission and reception are not great because of little antenna and being held inside a vehicle. Also, power output is a measly 5w. If you add an external antenna, mic, and power adapter, you end up with a bunch of wires coming out of it and lose the benefit of instant portability.
Moving to a basic mobile radio gives you 10x the power and with a modest external antenna, you've got the ability to reliably talk with distant repeaters as well as the convenience of a real mic, big screen, and bigger buttons.
I've tried both and though I still carry my HT in the Jeep in case I need it, the mobile really is the way to go when you've got one hand on the wheel.
Regarding the dual receive/crossband repeat features, I liked the idea too and bought a Yaesu 8900 (the big brother to the 8800). I ended up finding it too distracting - multiple signals coming in at once, small-unlit buttons, and it had way more capability than I needed or could use while driving. I gave it to my father when he earned his license and went back to the 7900. (big backlit buttons, fewer knobs, cheaper to replace if it gets stolen, fewer things to go wrong, etc)
I've owned and can highly recommend the FT1900 ($140) for 2m, the FT7900 ($300) for 2m/70cm, and the FT60 ($150) for portable, dual band use.