i have the 30gb 5th generation ipod video. it's great, i think apple worked all the bugs out, and i've had nothing but great customer service from apple between my laptop, ipod, whatever.
this year for christmas, i got my dad the zune because it has a tuner in it too, and he enjoys the radio. i remember him having some difficulty setting it up, but now he loves it.
you're bound to have problems with whatever you buy. just get insurance for 60 dollors or something and you're goilden. nothing that is manufactured in this day and age is flawless.