Just some anecdotal experiences.
Buddy has an Alpine digital media only head unit with on screen pandora control for iphone. It's nice.
I have a high end ~2 year old Alpine cd player in the Cherokee.
And a ~3 year old Kenwood Excelon deck in my Miata.
I much prefer the Kenwood over either Alpine. The menus are easy, it doesn't look as gaudy, and it sounds awesome. Granted I do have better speakers in that car than I do in the Jeep, but the Jeep speakers are being powered by a matching Alpine amp, so I feel like it should be closer than it is.
I probably won't buy another new Alpine deck. I will probably buy another Kenwood.
That said, some of the low end Kenwood stuff is pretty awful. (Have one in the Escort and it sucks.)