The reasoning for my emphasis on the song rating is due to the size of my music library. Even though I have a 32GB iPhone that's still not enough space to sync all my music. My solution is to only sync music that I have rated 4 or 5 stars.
Me likewise, except I have a full 160Gb iPod, and in recent times have started removing stuff, using a range of criteria.
I applaud your fine attempt, but we obviously listen to our music differently. I tend to just get stuck listening to my iPod most of the time, so not including stuff that might grow on me, is very limiting to my mind, and even with your program, it would still be a heavy workload to rate songs ... especially as I know many would cause me to umm & aah big time, which would give me a mind-bender and reduce my musical pleasure.
I tend to be an album, rather than song listener, but I do indulge in creating all types of playlists, based on all sorts of parameters (mood, etc).
Still trying to get all my Various Artists material completed, which would then put me into a better position to listen more to song based music.
The problem is I've only rated half my library and that has taken 5+ years. I listen to music most of the day at work, but get focused on what I'm doing and forget to rate the songs. That's why I wrote this script.
I've also been working on my library for several years (& more when I consider earlier organizings). I'm very methodical (as George knows) about my tags, artwork, ripping & loading etc, so I've written many helper programs myself, that are tailored to my specific needs ... still takes a long time but.