I've stumbled around the issue of live recordings and MP3's for a while. I have not expended a lot of brain power on it, but some of the ideas here make me want to look at it again.

I hate the little pauses "gap-less-less" playback creates, but I also don't like the harsh transitions that occur when a live track gets mixed into a random playlist. (It also bugs me when the intro to the next song gets tagged to the end of the previous song... but what are you going to do?) My solution to this has been to record one full MP3 and several track based MP3s, with my own fade-in and fade-outs. Really messy...

I'm not a big fan of crossfading, but that would have some interesting uses... I used to have a radio show and one of my gimmicks was the "dream concert." I would play a series of Live songs by different artists. If I was quick enough to crossfade the crowd noise just right, it would sound like they were all on stage together... Pretty fun. If I was really clever, I remembered to have a large gap of crowd noise (usually found in the first or last track in a live album) to toss in the station id. Made it sound like I was MCing...

Anyway, I'm just thinking out loud... This BBS has made me rethink a lot of my organization plans.