Like many here I don't think much of PMM. Dunno if this is an obvious solution, but I use MediaMonkey to manage my MP3 library and create playlists.
MM's playlists are robust and extensible. Dynamic playlists are supported as opposed to half-finished. Once your playlist is built in MM just click on it to rebuild and Ctrl-Enter to add the tracks to the Now Playing. In this way you can set up several dynamic playlists then combine them.
Transporting playlists from MM to PMM isn't difficult; it takes just a moment per playlist. I think this will work with other music managers that can save playlists as M3U files.
Start MM and build a playlist in the Now Playing.
If you prefer to pre-shuffle the tracks, right click and pick "Randomize"
Right click a track in Now Playing and select Save As. Pick "M3U File" Do not pick "Playlist"
Save the playlist file anywhere you like; I use my MP3 folder (Note: an M3U file is a small file containing a list of tracks)
Open PMM and scan the above directory for playlist files; the playlist should appear in PMM
Drag-n-drop the playlist to your DMM, sync and eject
I prefer a random selection from all genres, 500 tracks broken into 100-track playlists. The only playlists I use PMM for are By Genre auto playlists.
Not exactly a replacement for PMM but a workaround.
