We're probably seeing the effects of condensation during prolonged periods of disuse, even the gunk in the cover. Consider obtaining a good quality gauge for compression and check the calibration of your homemade leakdown gauge so you, and others, can have confidence in their results.

An Italian tuneup—as you have suggested—might sort out this Brick. Stranger things have happened. 

alright I'm done

Hi MEZ , wondering if you resolved your issue? Im thinking of converting my cable to hydraulic as well.

I drained about 8oz of oil and it does look like there is a bit of coolant or something in the bottom of the jar.  The bike is on a very slight incline so having drained oil from the top of the site glass circle to a little below center, hopefully that's most of anything unwanted.  I'm getting spark on all three cylinders and even tried the old plugs from my other brick, but it just turns over.  At least it turns over nicely. 

Compression and the fuel delivery next.  Maybe compression first because it's fast and I'd like to know why the seller mentioned a head gasket in the ad.  Hopefully clueless instead of coy?

On the plus side, I was led to believe the bags were on a different key.  Turns out I got two folding keys and one regular and they fit all the locks (though two bag locks are missing), so yay!  I also got in and out of the DMV fast (!) for only $59 for non-op when the online calculator primed me for a $390 hit, so shout-out to the PO for not letting the reg expire. 

The only hiccup was the DMV guy spelled my name on the title with an n instead of m.  Upon noticing at home (of course) the DMV chat person said I could get it fixed only in the office and once the title arrives by mail, so I typed "thank you" but was actually thinking "No thank you."  Close enough. 

I noticed there has been a little bit more dripped from the weep hole since yesterday. 

I gave the coolant hose that runs through the crankcase cover some squeezes and I didn't hear anything that would suggest there was coolant in there, which would explain why the jug of coolant was still 2/3 or more full.  So I pulled the hose at the pump and got 10-12oz of pale coolant with some crud, a stale smell and a bit of oil.  For comparison, I got about 16oz from the overflow tank so I don't think the PO bothered to refill the system, or just thought he did.  Does the pump burn up when lacking coolant?  Might be good that it didn't run for him. 

I just did the actual math - the title says 32,068 and the odo shows 32,086, so the PO got all of 18 miles of riding before things shut down.  What a bummer.  For him.