I started using Winamp in 1.x and 2.x days, then moved iTunes 12 years ago (before it had smart playlists, before there was a music store). It was simple in those days and just worked. During those 12 years it started adding duplicates, losing track of files, and even destroyed all of my album art with the latest Apple Music upgrade. It became difficult to manage. I wanted to get back to the days of "songs are just files on disk". Yet I didn't want to give up the organizational features. I evaluated Media Monkey, JRiver, Winamp, and a dozen others. All of them lacked something.
In the end I think I will go with MusicBee because:
MusicBee is the perfect balance between minimal, yet fully-featured, light-weight, yet customizable. Custom tagging, library and ui customization is fantastic.
MusicBee handles playlists exactly how I wanted: as .m3u files on disk, yet with library integration!
MusicBee's interface starts out simple and uncluttered, yet it offers every feature I could dream of under the hood.
Portable install means I can use a single USB thumb drive or android music player between work and home. No running servers, no clouds, no syncing (I've tried every combination you could think of). It just works. It's all local.
As a long-time computer user (25 years), I love the old-school simplicity vs. new-school feature balance MusicBee strikes.