You may try to enqueue in Winamp a whole and large collection of music contained in a folder divided in several subfolders.

If upon this operation Winamp crashes, most probably you have shortcuts that connect two or more subfolders in a way that creates a circle, making Winamp to try to load and reload ad infinitum the same folder.

To overcome this problem you don’t need to search for the shortcuts that cause the infinite reload circle, even destroying connections you may need to keep between folders.

Just create your playlist using a third party freeware such as the Playlist Creator, then load the created list in Winamp to continue editing or just to listen to it. Enjoy!