As far as I am concerned, there is nothing wrong with your engine.
You will have to go back and readjust your valves, though. The clearances in the book are for a stone cold engine. These clearances change when the engine warms up and metal bits expand with the heat. You can expect a noisy valve train next time you run it, unless you readjust the valves cold. And, there may be some concern about valve tip or adjuster tip battering over the long haul with excessive clearances.
I don't know why you are so intent on finding more problems.
If the rings are leaking cylinder pressure, the oil will seal the rings to make the pressures temporarily higher. An engine properly worn in at operating temperature will have the best piston-ring-cylinder fit. Adding a temporary oil seal won't improve it, as your tests clearly show. If you add enough incompressible fluid in the cylinder, the pressure will, of course, rise higher.
If you can find standard sized rings for the 550, you would also have to hone the cylinder walls into a cross hatch pattern, and follow a break in procedure to get the new rings to seat correctly. Both honing and the break in process removes metal from the cylinder walls and accelerates the cylinder wear. It's not hard to imagine 5-10K miles being removed from your engine life with just this process. You would have to measure the cylinder wall wear before and after the hone to to see how close to wear limits you are before returning to service.
Most likely you can't find Std sized rings. And, overbore pistons and rings aren't too easy to find either. Now you will have to bore and hone four cylinders to match the new pistons size. You also have to find a machine shop that can bore straight and accurate holes without removing too much metal to fit your new pistons properly, too.
You can go ahead and do a top overhaul on your motor if you want to, of course. But, unless that oil weep is severe, I'd leave it alone until you decided the bike is worth a $500 top overhaul.
If you absolutely HAVE to have a bike with no oil weeps, then disturb as little as possible with your currently fine running engine, in order to get it oil tight. However, while essential, new gasket installation is NOT a guarantee it will become oil tight. Cleaning and assembly techniques play a large role in making an oil tight engine.
It's not rocket science. Lots of people attentive to detail can perform this task successfully. Only you can judge your own skills and prowess. However, I would hate to see you trade the misery you have now for a bigger misery afterwards.
Good luck!