TBH I have tried zunes, iPods and generic mp3s, and I do like iPods way better, WAY better, obviously they are more pricey but hey, you pay for what you get. . .I ran through 3 generics in a year, after X time, boom they dont play anything anymore and they just become a storage drive. . .
iTunes, at least compared to Windows Media Player is way WAY WAY better, I havent used winamp enough to actually have a decision comparing both, but since im happy with iTunes, theres no need to try it.
BTW, what I do is open iTunes when I boot my computer and I dont close it ever, I just minimize it, and you can download the remote app fro the ipod touch and control itunes and your PC media from the ipod (works great to start up your day with music before you get out of bed)