Car nuts...what would be a better GPS system?

[Kaido]

I'm playing around with ideas for a better GPS system because I'm going to be traveling a lot later this year. I currently use a PDA with PocketMap. I really like PocketMap, but it's not a dedicated solution like a Garmin GPS and tends to freeze, be slow, etc. I am looking at two options. The first is the Garmin Nuvi 360, a hand-held GPS device:

http://www.garmin.com/products/nuvi360/

Pretty slick. The second is a laptop-based GPS system. Bluetooth GPS receiver + MacBook running Windows XP + GPS software. What's the best GPS software for driving? There are so many packages out there I don't even know where to begin. I'm sure some of you have experience with GPS stuff, so please chime in.