I’m always on the search for a good Windows mp3 player which manages large collections as I currently have over 22,000 songs (which apparently is over 96 days of music), and I’ve finally found a player which I’ve switched to; musikCube. It’s not quite as polished as Winamp, but it’s the first program which has been able to index my whole collection without crashing which is an impressive feat in itself. It uses a real embedded database, sqlite, to handle the data storage and seems to be able to track and update large collections with ease.
Through it’s plug-in architecture it also supports iTunes style ratings, and in general I must say the interface reminds me a lot of iTunes. Admittedly there are some wonky interface things about it that I normally wouldn’t tolerate, but I’m okay with them being that it is able to manage my whole collection and doesn’t take too long to index, search, etc. I also think the Playlist exporter could stand some improvement as far as the HTML export works; luckily it’s open source so I might have to dig into it sometime.