silicon O-ring lube and a plier does the trick for me; they have those extended tips for that very reason.
The cork rail gaskets only fit one way.
I don't use the cork gaskets any more; but when I used to;
I would
sparingly
glue them onto the block with 3M contact cement.
The ends of the gasket need to go where they belong, and a daub of RTV where the cork meets the rubber. If the rail gaskets are too long, you diagonally slash the excess out of the middle somewhere and another daub of RTV.
The pan must be sealed
because
if your PCV system fails, or it becomes overloaded, the engine will become pressurized, and the pressure will try to get out thru the weakest place. Better it is if the pressure blows the dipstick out, or lifts the valve covers, than that it escapes out the pan. It's just way less inconvenient if she blows out the top somewhere.
IDK about any overhanging cork tab.
360 rail gaskets are different from 318s, at the rear main.
Wait! I do know about the cork tabs; but I forget where they interlock; check the rear main cap, but IDK