GorillaXI
Never had a problem. I have had 2 Ipod's, an Iphone and an Ipad. Set up my Dad's Iphone and my Mom's Ipad. Not once have I had a problem. I guess it must be operator error.
On the other hand, I would never buy/own a Mac.
I am extremly well versed in all things electronic. I have a totall of FOUR iPods and will post a pic of them soon. I have used Winamp with the iPod plug in and it totally rocks. Drag and drop and done.
I have used media monkey which was designed for videos and it behaves much better than iTunes and can be used to sync iPods easily.
I have used Floola and while it is a very BASIC media mover it works at least as good iTunes.
When I rip a CD I use Exact Audio Copy for extraction and Lame to convert to mp3's. I usually keep all files as wav's because I can hear the difference in just about everything short of 192 bitrate. So as far as operator error it's possible but highly improbable.
The reason for four iPods-my family knows I'm into music and get them as gifts regularly. I also own two Samsung clips.
I would also like to note that thru this thread multiple people, truely the vast majority, see it my way. So as to your point I see a total of TWO who like iTunes. Truely fortunate enough to be able to use iTunes with no problems.
Side note: Do a search on iOS5 and iTunes.