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rob said:1) Probably nothing, but worth a look. Compression test is good, and you should probably do a leak-down test as well. It could be a trickle of oil getting past the rings. Have you tried sniffing? Does the smoke smell like burnt oil?
4) Define "runny oil filter." Is it leaking around the threads? My SS was doing that too. I never did find a direct cause -- at first I thought it was the Perf-form filter I was using, but switching to a Ducati-labelled filter didn't help. Shortly thereafter I discovered my piston rings were bad and that my oil breather was leaking as well. New breather and new pistons & rings, and miraculously the oil filter stopped leaking, too. I can't explain it...maybe someone else can.
If the "runny" filter is somehow related to bad rings, though, that might mesh with the smoke from the vertical cylinder. Seems odd to have the rings go bad after so few miles, but I suppose stranger things have happened. The leak-down test should flush that problem out, if indeed it is a problem. (As an aside, my SS had 36K miles on it when the bad rings were discovered.)
Bad rings= Blowby.......Blowby =Increased crankcase pressure=overpressure on seals...like around oil filters, ect. Which would explain smoking and oil misting around the filter. Plus, check the airbox for lot of oil...overpressure can cause blowing oil from breather into airbox.