Dans, Looked after a bonnie for many years. You say your new to these bikes

To own one you need to make a choice. Get a good mechanic and spend dollars or learn the art of zen and motorcycle maintenance.
For the latter you need a good manual and tools, especially a torque wrench to suit the specs for your bike. 5 ft lbs to 80.
Oil leaking from the head bolts could mean your head gasget is leaking or you could try re torquing the head.The black oil could mean your running rich or your rings are worn, there can be a few explanations.( still should not be leaking, that to me would say strip the motor and rebuild, what colour are the plugs ?)
Yes wet sumping can be a bit of grit in the oil pump as the scavange side of the pump should pump the oil out faster than than it is delivered to the motor. Its a problem when the oil in the sump is not pumping out fast enough and you start smoking.
When you drop the base of the oil in frame to change the oil , it is very easy to get a speck of road grit in the oil pipe if you disconnect it. Has to be very clean if you remove the lines.
There is so much but these bikes are very forgiving , just need to get to know the mechanics of them throughout.
The oil seals on the pushrod tubes can be tricky also if you remove the head for a look.
Find a good trumpy mechanic and give it a good once over.
Maybe simple fixes then ride and ride while you contemplate a rebuild as that will come.
cheers
Murray