iTunes for Windows can do random Shuffle > Album.
I've never used it, I've never used iTunes on Windows for playback at all, but the option is there.
You add the artwork to the files/album in iTunes, so I'm not sure that fits with your folder naming - again, I don't use iTunes on Windows aside from backing up various family devices, so YMMV, it certainly plays all the file options you mention, and does playlists.
Mark