One of the reasons I got an Empeg actually was to be able to only encode the things I like, so I wouldn't have to use the skip button as often.
I would love the possibility of being able to listen to an album and then just buy the tracks that I like. It's not because I like an artist that I like ALL his tracks. eg. I'm a big fan of the Dire Straits, but a track like "fade to black" is simply not my cup of tea...

I have wound up making some of the same decisions, but I start out differently. I tend to ripcode *everything*, let it come up a few times in shuffle/random, then I delete only when it occurs to me that "Yikes, I really don't want that on my Empeg". The good thing is that I've been re-exposed to songs I'd forgotten about or which I realized I actually did like if they were part of the right "mood mode".

I'm with Loren, the possibilities are just starting to come to me in part due to tools like Jemplode. I keep wanting to clone my #1 unit to a backup, but keep procrastinating while I debate more playlists!