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Other than the missing oil you measure, the rest to me sounds like a bad final drive seal. (The big one you see when you take the wheel off). Mine failed recently, and oil was all over the drive shaft tube on the swingarm like you describe, all over the rear wheel, inside the fender, etc. You can post stuff like this (questions) in the general section. Maybe a moderator can move it.
I tilted the swing arm assembly forward and a fair amount of oil leaked out. It has a vented cap with a plastic tube routed forward then around to just past the shock upper mount. What does the sealing? From the parts blow out diagram I only see a couple gaskets referenced.
I have successfully replaced that same seal on mine externally like that, so I would say yes you can.And good logic on the boot-off test. Actually, makes a lot of sense to me.
HiDid you ever find this leak?