Ok, I'm a linux user... my answer is..... 42!!!!
All I have to say to that is ROFLMAO.. if Spider Solitare is your thing..
http://www.semicolon.com/STDX.html
Get a Mac version!!!! Support OS X software developers!!
As someone else here mentioned Pink Floyd and iTunes do not play well.... just try listening to The Wall or Wish You Were Here or Final Cut... *music plays* bloop *next track* /me smacks head against wall.... I'm working on migrating away from iTunes for everything except purchases.. still wish Apple offered something other than AAC though....
I think iTunes has some flavor of crossfade, dont own a pod so I dont know how that translates over...
As far as rockbox is concerned the one thing holding me back from an iPod besides the herd mentality is the lack of other codecs. AAC/MP3 is nice an all, but I do have some FLAC and a fair amount of OGG, not to mention some really oddball stuff from old computer games and such that no player ever will be able to hande so I just transcode to MP3.. midi support would be kinda cool too, but now I'm really dreaming!