Yeah, there's a leak. Working on it. Cleaned under LH crankcase cover, and under engine as it was too grubby to track the leak. I was going to run it then then get back under cover and check the source, but alas, not starting, so no leak chasing. Clutch pushrod seal looks like at least one likely source though. What that means for repairing I have no idea yet.
As for the starting, I plan on putting up a build/rebuild thread tomorrow where I go over the list of things to be addressed, and what makes sense considering the build plans. But in short, from what I've read and seen so far, my money is on a stator issue or bad battery issue. It used to start okay, then it seemed to only be on second start it'd go. Electric start--I hear it trying but no final turn over. Then the other day, I could only get it started with the kick, same next. Now nothing either way, and no headlight action as of today--charged battery between attempts. Battery doesn't seem to hold a charge as long as it should, even when bike isn't being used. PO said battery was new (but who knows if he actually kept it on a tender--I doubt it); it's not OG acid batt. Mechanic who changed the tires actually tested the voltage before test riding it--12.5V at idle, and then 12.4V@ 5k RPM. So from what I understand sounds like it's not the regulator otherwise the voltage would be flying away way high at that 5kRPM; sounds like it's actually not charging the battery. I just bought a multimeter today so I can go through the system tomorrow; going to look up how to test stator; so far only seen rotor tests for OHM. In the meantime, the battery is on the charge tonight.