Lifehacker is proppin' this app MediaMonkey as an MP3 management app.
In the comments, a guy propped the open source/free app SnackAmp, & claims the app developer replies to emails with questions/bugs/requests/etc.
Windows Media Player stays crashing on me, so I've been using Foobar for playing mp3s & playlists. I might check out these other apps at some time.
As always the pain/time of investigating something that might be better, vs the limitation of the existing app/process.