I think this is getting a little confusing for a novice. Kicker keeps refering to a pin on the cylinder but is is trying to tell you that there is a small pin on the piston(not cylinder) that keeps the ring gap in place. Also the rings must be installed the correct way. If you are using OEM rings and pistons the top ring is obvious that it can only go one way but the bottom ring actually has a taper to it and must be installed the correct way or it will not go all the way into it's groove and be too tight in the cylinder. All rings that are directional will have a very small stamp on them, that stamp should always face up. It is on the flat part of the ring, sometimes it is a dot, and "R" or a square. That mark should be facing up towards the cylinder head. I think this might be why your cylinder will not go past the second ring. You should be able to do this by yourself.
1. Apply a light coat of injector oil to the cylinder walls.
2. Make sure your base gasket is installed.
3. Install rings correctly on piston.
4. Make sure cylinder is facing the correct way, arrow on piston faces exhaust.
5. Hold the top ring in it's groove and aligned with th pin with one hand and lower the cylinder with the other.
6. Repeat with the second ring.
7. It should go on easy with no force. If there is resistance stop and determine why. Do not bend a ring.
Finally do not spin the cylinder if it is a little twisted on the ring, you can break the ring. If it is a little off you can rotate it while sliding it down. To clarify only rotate the cylinder on the piston while it is moving either up or daown on the piston.