sounds like you definitely need to investigate the problem with the bolts. If they arent clamping the head down like they are supposed to, that could cause your oil leak both ways for sure. Are all 4 bolts the same length and diameter? In my limited experience with v twins(actually a v twin lawn mower wont lie
) a couple of the bolts are short to clear stuff on the intake valve side of the motor. But that def doesnt sound normal to have to put that much torque on head bolts. They should be nice and clean and thread in most of the way by hand. The head is pretty much the only place oil can go into and out of the motor easily