This is how I have used WinAmp for years. I have folders for each artist, and within them, folders for each album, and then the actual tracks are in the album folders. Sometimes I have several sub-folders for an artist. When I right-click a folder, I want to play EVERYTHING within that folder, including all sub-folders -- that's why I clicked there!

To illustrate, I have the following folders:

......City of Light
........Hallucination Engine
........Memory Serves

When I right-click and choose "Play in dBpowerAMP", this is what should happen:

on "Music", it plays EVERYTHING
on "Laswell", all Laswell folders and sub-folders
on "Material", only the Materal albums by Laswell

and so on. And of course, if "Random" is on, it should shuffle all of the above :-) You get the idea. With this system, I have managed with WinAmp, as I said, for years with no type of library software, by going through my folders and right-clicking "Play" or "Enqueue", as desired, to create my own on-the-fly playlists. With dAP & MMC, I now have a much, much better system, but I have lost the ability to play multiple folders. And because I change my folder structure often, creating playlist files is not a good solution (and too much work to depict something that's already there in the folder structure).