After blowing air through everything again, I replaced the tinwork, filled it with oil and started spinning the oil pump with my air drill. IT PUMPED OIL TO THE TOP OF THE BLOCK THIS TIME! It didn't shoot out like I had expected, it just oozed. That's a lot better than what I had, though. I had a spare #848 head that I took to the machine shop to freshen up. The stock head that I removed from this '58 was a # 913. The 848 had smaller combustion chambers, so maybe it will help it a little.

Thank you all for your input on this! I'll put up some pictures of this thing soon.