So.... here is an idea for a plugin for Winamp.
You could have an optional window that would let you dig through a "virtual crate" of records.
This mode / window would take the picture meta-data for album art and turn them into a 3D square representation of your albums and you can flip through them just like if you were at a record store looking for new vinyls.
Yeah, I know Winamp already has the nice resizable "Album Art" screen, but I think there is potential in a "Record Crate View" like I am describing.
Hell, maybe you wouldn't even need to make a "crate" but just have a window that has 3D square panels lined up like the Windows Key + Tab view, and then you just use arrow keys or mouse or whatever to flip through those.
A more complicated, albeit cooler idea would be able to set up a whole wall-shelf sorta thing where you can place records into shelves and have stickers which you can type the genre onto.