orphanespresso wrote:Stugi's feeler gauge idea is pretty good, hadn't thought of that one, but then Stugi has things pretty well figured out.
It's a trick I've learned from installing piston and oil rings on pistons in combustion engines, if it works on rings made out of steel, it should work with rubber rings as well.

It takes some practice though, but it has the benefit that you can block any grooves that the ring/gasket can accidentally slip into, thus minimizing the risk of damage as Stefano pointed out, but with this method you only need to stretch the gasket a millimeter or so, and not over another gasket (which can be a tad or a lot thicker than the piston when seated depending on groove depths, gasket hardness, spring seals etc.)
If you combine this method with a lot of lube, it should be quite smooth once you get the gasket onto the piston. If you have to install several gaskets, slip on the first, set it on the middle of the piston, slide on the next gasket until all are on the piston. Then center them over the grooves and pull out the blades one by one slowly so both gaskets are seated at that particular spot before removing the next blade.