Here's my suggestion.
(1) Don't use WMP for music files like MP3 or FLAC. Use a true music player like Winamp
(2) Use MP3Tag
to clean up your music collection. This is a terrific highly regarded program that can tag all types of music files, deal with both imbedded and external album art, etc.
(3) Put all music tracks for a physical album in one physical folder, whose folder name is the album name. You should also collect all your physical folders for albums by a single artist under one single physical folder for that artist.
In other words, your music collection should be organized as x:\Music\Artist\Album
(4) Remove all internally imbedded duplicate album art JPG's inside your MP3/FLAC file tags in each music file using MP3Tag, putting just one of those JPG's into the one physical album folder for that album in which all of the music files from that album file live. Name that one JPG as "cover.jpg".
This one "cover.jpg" external album art JPG will now be used by Winamp to display as the album cover art when ANY of the music files in that physical folder is played. This makes intuitive sense, as it's one album, should have one album art image, and should be displayed whenever any of the music files from that album are played.
Winamp has an "Album Art" window in which the album art for a music file will be presented. If there is an imbedded internal JPG in that music file's tag then it will be displayed. But if there is no imbedded JPG (as I'm recommending), then the external "cover.jpg" image in the host physical [album] folder is presented instead.
(5) Winamp will display the internal tag values for (a) song title, (b) artist, and (c) album title in its player and playlist windows. To avoid confusion your external physical album folders and physical artist folders should have the same names.
==> The use of a single physical folder corresponding to an album is the recommended organizational method. The external physical name of that folder should be identical to the internal "album" value in tags for each of the music files stored within that folder, to avoid confusion as to whether you're looking at internal or external "album" value. If they're both identical, it really doesn't matter which is being displayed (but I'm telling you it's the internal tag field value which is being displayed).
==> You should not imbed album art within tag data of music files, as it's unnecessary duplication and wasteful as each music file for the same album will have the identical imbedded JPG. Why do that? If you already have a collection that has albums as your lowest-level physical folder anyway, just eliminate all imbedded album art JPG in tags and instead put one single album art JPG in that folder along with the music files, with that JPG file named as "cover.jpg". Winamp understands what "cover.jpg" means and uses it exactly as I've described above.