If the rings are goosed you are correct. You would see oil burning.
There would be smoke in and around the PCV valve as well and your also correct. If the rings are pinched, I believe there would be sooted plugs as well.
Get the head checked at the shop and go from there.
Al.

 

Thanks for the feedback. Now the machine shop is closed till Monday. Anything I can do to verify the valves sealing on that cylinder? Any way I can check the valve train aside form a cursory inspection? How can I get a look at the lifters?

Update: Went to the dealership for more gaskets/bolts. Apparently now I get wholesale on whatever i want according to the parts guy. Bought a bunch more parts for the other side since it was a good deal. 84 cents a push rod is nice, brings light to an otherwise dark project.