... isn't the cylinder supposed to be narrower at the top?...
Only on large-displacement, large-bore air cooled aircraft engines.
This is far too much oil intrusion for fresh rings, guide seals, head gasket.
I'm thinking warped head, microscratch on mating surface (don't drag precision machined surfaces across pebble surfaced patio floors), or the rare casting porosity problem, possibly pinhole in intake port. Porosity/pinhole(s) can be found by doing the valve leak test, on a very dry/clean head, with the solvent poured into the intake port(s), and looking for solvent wetness in cam area.
We would check head surfaces by using a very flat sheet of plate glass, smear on a thin layer of fine valve lapping compound, then quick lap (moving head in figure-8 pattern), clean, inspect. Look for untouched surfaces and micro scratches. If significant, have head resurfaced, else, finish lapping.
Whew, feel like I'm full of tea, switched to coffee...