Hello Peter
The packing needs to just standing a 'bit' proud, but it will be all over the place with high spots and hollows. Once it is in the bore it should even itself out. Yes you want to be able to 'just' pull and push the piston gripping the piston rod. It will be tight so oil it.
Make a conical adapter (5-10 deg internal taper) that you feed the piston and packing into, then line that up with the cylinder bore to easily slide in. The inside bore of the adapter exit should be the same as the cylinder bore. The taper helps squeeze it all into shape.
Norm