Kernel not recognizing your hardware? Problems with power management or PCMCIA? What hardware is compatible with Gentoo? See here. (Only for kernels supported by Gentoo.)
I was wondering, is it possible to start gtkpod start when I plug my iPod, ala Windows? You'd have to pass the Xserver as an argument, and write a script to execute when the iPod is plugged in.
I am not sure about this, but I am sure that gtkpod is very much better than whatever it is windows uses (jukebox or something?) check out easytag also, that program is a great companion to gtkpod.