I've always thought of AIMP (https://aimp.ru) as the modern sucessor to winamp. It has that braindead ease-of-use, with a lot of pretty impressive functionality and integration easily accessible from a standard install. Foobar is the choice for ultimate customisation, but i gave up trying to achieve what was present in a basic AIMP installation, and in several years of playing, coverting and tagging, the only lasting changes ive made are the installation of one skin, occassionally selecting a new highlight color for it, and initially pointing it at the directory containing my LAME binary, and dictating my file naming scheme for transcodes.