Well now...
So, turns out it was user-error that caused my issues the other day. :facepalm: :mad-new: (No real surprise.) I am sure other ring compressors work better, but once I figured out why the ring broke last time, it went so much easier. I had been thinking it was a little strange that the rings could just rotate around the piston so there's a chance of the gaps lining up, which would cause problems with compression I would think. So while I was looking at things today, I noticed they had thought of that. I'm sure y'all seasoned engine tinkerers already knew this but this newbie didn't. :wave: There are little nubs in the grooves where the rings sit, preventing them from rotating! So once I figured that out, I was able to get the compressor to properly compress the rings, and viola! So now my theory is that the ring broke because I was putting pressure on it with the compressor while the nub was in the wrong place. Live and learn. Luckily a new ring isn't expensive, but I do have to wait for it.
A question though, I realize there should be a rather tight fit in the cylinder, but should I be able to pull the piston back and forth easily, or should there be quite a bit of resistance? I used some assembly lube on the walls and piston, and later added some 4-stroke oil on the cylinder walls. But it takes both hands and quite a bit of force to move it. Would this be an indication I need to hone the cylinders?