Hi - I get all of what you're looking for with my Oregon 400T. Its biggest issue is with the screen but I've got used to it - it's best if you actually get the light reflecting off it. The 550 is supposed to be better but I haven't seen it. BTW, battery life doesn't seem to suffer with having the backlight on all the time, and the brightness up full - it certainly serves me all day - and with spare AA batteries in my bag I don't see any issues.
I get the driving directions by adding a (Garmin) SD card. That's the easiest option to go for but functionally it's best to get the maps on DVD, to download to your own card (this leaves the rest of the card free to take other data etc.). Because the Oregon allows for different profiles it's easy to switch from geocaching mode to automotive mode. BUT, as someone else has replied, I agree that a dedicated vehicle SatNav is preferable.
hope this helps
JsR