I got my brother a Garmin Nuvi last year and he loves it. He's kind of a fucked up driver like you (navigationally challenged?) and it works out really well, especially in the big cities where he gets lost pretty easy.
http://www.amazon.com/s/ref=nb_ss_gw...n+Nuvi&x=0&y=0
I don't remember which one it was...probably the 350 or 360. It meets every one of the points you're looking for and I've used it once or twice and liked it.