I love my 5.5gen Ipod, it's the only pod that can hold my music, it's based in my car and i use my itrip with it, no faults. I have a shuffle for the gym and my iphone for everyday walking around, but i dislike the fact that i have to switch music around if i fancy a change!
I love the fact the ipod was transformed into the 'classic' and the storage keeps going up, but with the ipod touch, the iphone and the nano taking the limelight the classic does seem a little oldschool for todays market.
A refresh with HUGE storage, possible 3.2mp + camera/HD Video, larger screen, BT/wifi file transfer and similar applications to the nano - nike+ integration, pedometer, FM reciever and possibly an FM transmitter??? Would definitely make the oldschool ipod fly off the shelves again!
Although of course i'm dreaming, next update will just be bigger HDD!