Alright, a lot to catch up on now that the holidays are over

In short:
I believe what happened was I washed out my piston rings from running it too rich. I wasn't aware that this was a possibility and I knew there was a danger in running too lean, so I purposefully was running fairly rich ever since I got it running (about a month ago).

Long story version:
I drove my car to a local tuner. I know people that have used him and I trust his work. We talked for about an hour, I gave him all the details and everything I've done. At this point, my car smokes a lot from the leaking oil as well as the excessive blow by. In his opinion, my ring gaps alone wouldn't cause this issue and after talking more he's confident I washed out my rings from running it too rich. I got my car back to my garage, did another compression test with about 2 weeks and about a hundred miles on the engine since the first test. 2 of the cylinders were sub 80 psi, which told me, yea, I botched the ring break in. So, next week, I'll be putting in some fresh rings.

That being said, I appreciate all the advice here. Also what are y'all's opinions on ring materials and break in procedures.