No Ryan it's not rideable like that you will do it no good.
It sounds like it needs new rings and who knows? maybe even a rebore, the black marks are signs of 'Blowby', this happens with worn piston rings or a worn bore. the gaskets will need replacing, be sure not to get any debris into the crank case when removing all traces of the old one, stuff a rag in there while you clean it up.
I am concerned about this rounding...It isnt pulling the stud out of the case is it? I hope not as it would need a thread insert which is no job for an amateur,