Definitely the cover from what I can see. I stuck a Qtip in the weep hole and it's just some road grime. The leak is getting worse, though. I just remembered I left the bike in the drive with nothing under it and there was already a spot of oil an hour later with more ready to let go. I gave the three bolts a quick check and they're not too tight, but maybe previously they were over-torqued which led to the broken bolt by the PO. Maybe it leaked and he tried to snug things up a bit? Who knows.
I guess unless there's another suggestion, I'll just keep cardboard under the bike until I do an oil change and can give the cover a better look.
As for the clock, I think I'll leave it for now. Good vs Perfect and whether I want to potentially break something that's made of 33 year old plastic.