Yeah, but the problem I have with the iPod thing is that while 256GB is a lot more than 40GB, it's still only a fraction of my collection so I'd still have to s

Yeah, but the problem I have with the iPod thing is that while 256GB is a lot more than 40GB, it's still only a fraction of my collection so I'd still have to spend time deciding what to put on it. 40GB is enough to go months of normal usage without hearing the same track twice. So I have a python script that loads every 5 star rated track onto the Sansa (using up a good chunk of that 40GB) and generates an m3u of all of them, pre-shuffled. I feel like that's the best compromise I can make for having less than 100% on a single portable device and 40GB is plenty for that. More than 40GB and there's not real improvement for me up until about a TB.