Originally Posted by kogia
It doesn't seem to matter how I fiddle with the Shell Options, I can't change what left, or right clicks do, or what context menu options appear?
Sometimes it is necessary to reboot after making changes to certain parts of the Windows registry. This forces Windows to load and use all updated registry entries. There are other ways to force a reload of the registry, but rebooting is probably the best way to avoid introducing other issues.
However you have said that you have been trying various options and your screenshots show some inconsistencies. For example, you say you can double click on a file associated with Winamp and it opens and plays. But the "File Types" dialog shows that the "Enqueue files on double click" option is enabled. Also, the "Shell Options" dialog shows that the "Enqueue in Winamp" folder context menu option is selected, but the "File Types" dialog shows that the "Show Winamp actions in the folder context menus" option is not enabled.
Reboot, then download and use the "ShellMenuView" utility (http://www.nirsoft.net/utils/shell_menu_view.html
) to see what context menu entries are currently in your Windows registry, that are associated with Winamp and with the file extensions associated with Winamp. If you're using the 64 bit version of Windows 10, be sure to download the "for 64x" version of this utility (the download links are in the bottom quarter of the page linked above).
You may need to do a 'clean uninstall' (i.e. delete all of the Winamp program files and the Winamp user data configuration files and registry entries) and a fresh install, instead of reinstalling over the installation you already have.