I bet you anything I can figure this out. I solved a big issue I had before and posted it but no one cared! I also want this problem solved.
My last problem was that I wanted a playlist containing all of my favorite songs (rated 3,4,5) and the associated Folder.jpg file. This was QUITE a task but I did get it worked out. It allows me to copy music and the cover art for each album to my mp3 player and then see it on the screen. It only took about 15 minutes but I think that's because I happened upon thinking the best method for accomplishing my goals early on.
What you're asking sounds simple and if I have time this weekend, I'll work on it. Right now, I am working on a math assignment due tomorrow. If it was done, I'd work on this right now!
I really like your theory, too! I like how you should name all duplicate songs with the (Remix) thing. I do often follow this but it wouldn't be hard to find duplicates and add the necessary info like ( ). The biggest problem is finding out what version each song is because I have a lot of compilations and duplicate songs from greatest hits, etc., and sometimes, these are remixes and other times they are not.
After rereading your question, I don't really understand what you want to do. I was planning on figuring out what you wanted later when I was going to begin the project. Are you trying to create a unique songs playlist? Do you not want remixes, live versions, etc.? I