Okay, I've gotten some clarity on what's going on and what I'm going to do next. Brace for wall of text.
Re. the state of the machine, I'm in Vegas -- so no condensation or rain. The machine's also in very, very good condition otherwise. No detectable wear in the lead screw, and the two gibs I pulled looked like the scraping was untouched. I'm pretty certain the seller didn't bone me and the machine was very occasionally used -- just dirty from being in an auto shop.
For the bearings, they're NTN 7207C and NSK 6206V. I actually got a thumbs up from Tom Lipton on Acras (he has the variable speed model and has worked with other models,) so I'm not too concerned about being cheaped out by the builder. More importantly, the runout I measured before the spindle gooping was in the low tenths. And even if it's worse when under load, I'm going to keep using the ones I have until I'm unhappy with them, and then I'll just order from H&W. I'm hoping to avoid spending that money, but I'm comfortable installing them if necessary.
As for the plan going forward.. I've finally pieced together the puzzle. The upper bearing is shielded, and the lower bearings definitely had some grease in them -- so the assembler (I don't think it was anyone else; the nose cap had the set screw in the only drilled spot on the threads) went with grease, not oil. This also explains why the spindle oiling cup that's mentioned in the manual was replaced with a grease zerk, and the grease zerk explains the Nutella that's all over the top bearing. The oil that's visible is likely from me adding more than I should, in hopes that I'd flush out any tire dust that had accumulated.
So given all of that blather, I'm going to clean clean clean, repack the bearings, clean the inside of the quill, and be a lot more gentle with the two remaining oil spots. I also figure I'll need to pull apart the top housing and degunk what's in there, but that's for future me to deal with. I'm not super thrilled about pulling the motor off without help.