I'm trying to get the "Now playing" feature running with AdiIRC, which works fine with the original Winamp-release.
I now cleanly removed everything (with the exception of having used a registry cleaner) and reinstalled WACUP.
There is a special option to create a legacy file for making plugins work in other programs (AdiIRC in my case) under Options > Preference > Advanced > Options Page 2 > Playlist Compatibility which I had checked before and which is checked now.
I installed WACUP under C:\Program Files (x86)\winamp\ and set both paths in AdiIRC accordingly.
The m3u file is only searched if the proper plugins are installed and winamp is set as the current media player and winamp is running. There is one plugin for adiirc and one for winamp, Interop.ActiveWinamp.dll for adiirc and gen_activewa.dll for winamp.
the gen_activewa.dll must be registered with the regsvr32 command, AdiIRC tries to install and set all of this up when you change media player to winamp. It uses the path for winamp set in Options -> Media player to put the plugin in the correct place, but it can be a little buggy since winamp has to be closed etc.
Another quick note, the adiirc winamp plugin is not a plugin you will find in Menubar -> File -> Plugins, it just needs to be in the config folder and AdiIRC will automatically use it when necessary, the problems are usually with gen_activewa.dll which needs to be in winamppath\plugins\genactivewa.dll and registered in that path with regsvr32.exe.