Update: I finished assembling the motor last night/this morning (1:15am). To summarize up to this point: The engine was smoking, particularly as it warmed up. The head got new exhaust valves and seats were machined. Intake seats/valves were lapped. Ridges reamed on the cylinders, new set of rings installed.
I took some measurements using the diameter of the ring as a fixed variable and using the ring end gap to check the change in diameter (it is the ring end gap divided by pi, incase anyone else comes across this thread and needs to find cylinder taper and does not have a bore gauge). Based on the recommendations from Hastings, taper should not exceed .004 in. per inch of bore. Therefore, I calculated my maximum taper at .014 in. (3.6225 x .004). The most tapered cylinder came in just under that at .011. I deglazed the cylinders, cleaned them out, installed rings on the pistons, and installed them with a coating of Rotella 30wt on them and the cylinder wall. The bearings also got some assembly lube.
I immediately noticed a difference in trying to turn the motor over by hand using the fan. The belt would frequently slip without being able to turn the crank as soon as I got past installing the 4th cylinder. Once the head was installed, it was impossible to get the engine to turn over without the belt slipping. I hope to test fire today with positive results.
Lingering concerns: 1. The pistons had 7 piece rings installed. I'm not very experienced at all, but I have never seen this set up. It has a top ring, the second grove had 3 rings (one thicker ring, a thinner ring, and a heptagonal ring under those whose job seemed to be to keep outward pressure on the other two), and three oil rings (the center ring was more like a bearing cage than the typical wavy oil ring). Anyone know about these rings? 2. The con rod bearings have a bit of horizontal play. I didn't replace the bearings knowing I'm going to have to do a full rebuild soon, and I hope it is the wear in the bearings that is allowing this, but I would appreciate any input. The caps seemed to have been torqued pretty tight when I took them off and I am seeing some conflicting info on the proper torque. I have not filled the crankcase and would appreciate a torque spec for these before I do. (Currently set to 30ft-lb.)