I've heard from numerous people, on this forum and on others, that Alpine's iPod interface goes to hell if you have more than 255 songs on your iPod. I don't know how true that is, but if more than one person is saying it then it makes me wonder how worth-while it is. I prefer Alpine gear over Pioneer by far, but they're the only two options I'm looking at now for my Jeep, and if Alpine's doesn't work over any amount of songs, I won't be getting it..

EDIT: I like that Monster solution, thanks for posting that cgkaide!