Play Doctor is brilliant. And I never see it!!
I have assigned Ctrl+Alt+R as a global keyboard shortcut to "play Radio". I use library server on this PC, so the shortcut works, even if the main MC program is not running.
The saved Play Doctor playlists are superb in Theater View. If you switched your lists to saved Play Doctor lists, you would never need to manually shuffle them now and then, MC would take care of that for you.
In theory, a Play Doctor list should never end. It will start off with 100 tracks pulled from the search rules, and as each track finishes, Play Doctor will add another to the list.
I've tested, and can say that for me, when last location is Playing Now, and start playing current playlist is set as "Yes", when I close and restart MC, it opens in Playing Now, showing Play Doctor, then about two seconds later, playback begins and cover art is displayed instead.
Note that if your "Last Location" was Playing Now, and you were playing a Play Doctor list, when you restart, it is no longer a Play Doctor list. It reverts to being a static list that will stop when it reaches the last file. It remembers the list location, and there will be 100 files to play before the list ends.
Do you have a last.fm subscription? If you do, you can include last.fm tracks in your Play Doctor lists too, which is neat.
-marko