Been a while since I have used Plex’s API, but I’m sure it’s possible to use a user’s playback history to build a personalised recommendation profile to build playlists for those days when I’m not sure who I want to listen too but definitely want to listen to a particular genre of music?
On another note, I would so love to put a winamp skin on this.
Have you played with Plexamp already a bit?
You should have noticed the ‘Stations’ section on the home page. (you might need to scroll down a bit to get to it.)
Just play with it, instead of requesting that every menu item and feature has to be identical to existing solutions. You’ll soon discover that there is more in it, than is apparent to the eye.