Not DieselGman, but I will take a stab:)
Timing can be determined using a dial indicator and magnetic base to look at the opening of the intake valve. Place the indicator to read the downward movement of the valve. Not sure if the 8/1 spec is different, but on the 6/1, the intake valve stem should be pushed down(open) approximatly .020" as the flywheel reaches the TDC mark...
The cylinder liner on my 6/1 is beveled at the bottom. I don't recall needing a compressor to put the cylinder into the liner, just a small standard screwdriver to push on the rings a little bit into their groove to get things moving. Oh, and of course lube liberally. I install the piston and rod with the cylinder lying on the bench and push it all the way to TDC. I keep it up there using a large horseshoe magnet on top of the piston with a stick thru it. I then install the whole assembly ontot he engine. I put a little tubing over the big end studs to keep them from marring tghe journal. With the piston at TDC and crank at BDC, the two shouldn't be able to meet anyway. I find this easier as it is pretty tricky to manhandle the cylinder into position by itself, letalone get piston positioned properly into bore while doing this...
Why not do it from the top of the cylinder once it is inplace? I looked at this, but found it kind of difficult to get hand up into case access door to keep rod from hitting crank, and get piston pushed into place. If it starts moving on it's own after the last ring gets into the cylinder, it is pretty difficult to stop it with the limited access...
My .02 as always