Musicbee. That's what's used on my Windows side. Here's a list of features:

Manages all your media and supports a number of formats including MP3, AAC, M4A, MPC, OGG, FLAC, APE, Opus, TAK, WV, WMA and WAV.

Create and manage playlists, and "smart" playlists that update based on custom filters

Enqueue songs into a "Now Playing" pane for on-the-go playlist creation.

Watch folders on your hard drive for changes and automatically adjust your library accordingly

Import libraries from iTunes and Windows Media Player

Sync Android phones, USB drives, some iPods, and many other portable music devices with your library

Convert files on-the-fly as you sync to your devices

Auto-tag your music using the music databases of your choice

Keep your files automatically organized in folder based on tags

Customize a number of different keyboard shortcuts

Subscribe, download, and listen to podcasts, either by searching MusicBee's podcast directory or by adding feeds yourself

Use advanced audio features like a 10-band equalizer, crossfade, WASAPI and ASIO playback, and more

Customize your player with skins, different layouts and views, and three different players including a mini player and compact player

A plugin architecture that lets you add lots of functionality to the player, like extra supported formats, skins, library organization tools, and other features (Winamp plugins supported)

An integrated browser that allows you to browse for just about anything in-player (useful for browsing plug-ins, skins, and so on)

Hopefully that's helpful. Sounds like it's what you need. Requires a little tweaking, but once you get the workflow down, you'll find it irreplaceable.

On the Mac side I still use iTunes, because it works better with that architecture. Sometimes I use Vox if I want something more lightweight, but I love the album view on iTunes.