go back to basics, Now that the engine is off, pull the shroud and the head off the engine. If you had done a basic tune up in the past and it was running (and you still have fuel, spark, and compression) I would venture to say that maybe something happened with the timing as a start point. If it was running after the tune up but did some popping or backfiring it may have knocked the keyway loose and took it out of time or something to that effect.
Remember that when you did the points the first time you had to pull some head bolts loose to get the cover off, you just loosened up part of the head on a 45 year old engine with possibly the original crusty flattened out head gasket, so chances are good it would start to leak.
The head gasket needs replaced, so pop the head off and get a good look at the cylinder wall and valves at that point to determine if its all carboned up, or something passed through, etc. Now onto the flywheel, Is it still tight? when you remove it how does the keyway look?
The only aluminum flywheel Tecs (60's early 70's) that I have ever found to have a sheared or messed up keyway have been Fox HS40's on the 10" wheeled bikes......I am guessing it stems from the carb tuning. They are a finicky carb that does not like any type of debris in the system. so they get out of tune or dead spots and maybe cause a good backfire......keyway gone.
start there :thumbsup: Of course anytime you have the flywheel off its a good idea to give another inspection of the points, gap setting and that all the wiring is staying clear of the moving flywheel etc...
So even if you find something simple I would suggest (if you did not do it before) replacing the intake gaskets and the exhaust gaskets as well at this point along with the head gasket.