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I've not really been thrilled with my experience with rockbox. I'm thinking about giving it another try though.
Battery life does decrease at bit, but i haven't had the opportunity to run down my battery yet. My 30g used to get about 12 hours of listening, less watching. My 80g is longer, but i don't work the 12's like I did, so I haven't had the chance to really burn one down to see. This is stock ipod firmware though, not rockboxed.
I use videora as well. The price is right and the results are good.
I only use itunes to update the firmware. my wife uses itunes for pictures and we're starting to play around with videos a bit more of the baby.
I'm a fan of Media Monkey. It handles a large library pretty well. I can play tracks off of my player when pluged in as well as tracks from the library that resides on a separate physical drive in our "server."
Tried redchair and it worked for everything, videos, pics and music but then my 30g died. Redchair only allows one ipod per license and when I emailed asking how to deactivate one ipod for an exchanged newer model I never received a response.
I haven't used winamp. Never tried windows media. I'm pretty comfortable with media monkey on my back but as it is with all new software and love interests, takes some "get to know" time.
