Hi Marty, if you assemble the engines on the older classics right they will not leak oil. A 1956 T100 I recently restored did not leak any oil (pictures on the forum under classics), although they are a bit of a money pit when restoring them though. Sounds like you have a really nice machine, I have seen the Union Flag paint on a number of Triumphs and they do look great, I really like the two tone grey number, I'm waiting to have the belly pan on my 2020 RS done with the Union Flag. Ride safe all.