I lashed out and purchased a gen5 80 gb ipod. I tried it thoroughly for 6 months. Then I rockboxed it. Then I gave up. Utterly hopeless if you are a power user - because there is no power! I gave it to my extremely excited son. He tried too. It only took him 4 weeks to give it back. Now its for sale...
I have a couple of iRivers, which max out at 40 gb. Very old and clunky they are, but the software and its overall utility is just about perfect. Its funny, that these sell on ebay now for more money than a new ipod. I should know, I bought two more. Now I am searching for 80 gb HDDs to go with them.
We found the ipod to be perfect if you are a) computer illiterate an b) have only 10 cds in your entire collection (I don't mean this as a joke, it is good if you are small in size). I have around 25,000 and it cannot handle them. I can load my iriver fully in about 1 hr, just copy from my hdd with windoze. Thats all. To load an ipod with itunes is the most painful experience I know. The software is totally crippled. one album takes a few minutes fine, but multiply that by 1000 on an 80Gb drive. Then, try to find that particular album.
The one thing I like to do most with 1000 albums, is use random. The ipod does this well too (NOTE rockbox has NO random!!). However, when you hit the track or album I like, I want to hit one button that says "stop random and play this album, and when you finish, don't stop, just play the next album on the disc". This is simply the third button on my iriver, and a non-existent function on an ipod. There you have to note the artist and album and track, go back to the start, navigate a 1000 albums to find it, forget what its called, then simply give up.
So the ipod is fine (if you want no control). While itunes is an abomninable program.
...there, thats about the longest "speech" I have ever posted on a forum in my career...