Some cylinders have a lot of taper that allow rings to enter more easily and of course the more cylinders the more complicated. it is best to use piston supports which can be made from bent up welding rod( u shaped)or wood, metal, nylon, etc. these will hold the pistons square on top of the cases. There are different kinds of ring compressor designs, you will need one that will keep rings compressed while the cylinder is lowered, some compressors will allow rings to expand before the rings enter the bore (if your cylinder has a lot of taper) You really do not want to oil your rings for assembly, just piston skirts and light coat on bore , other wise you may have issues with your rings seating. Another method is to install piston/rings in the bore and then put the pins/circlips in after you lower the cylinder onto the studs..