The piston has a pin in the ring groove. It's supposed to capture the ring gap and prevent the ring from rotating and potentially snagging on a port. Was the pin and ring gap lined up during your struggle to get the cylinder back down over the piston? If not, safe bet you have a broken ring now, if not before.

On another wavelength, this is the rear carb version? A broken or hung up reed valve can cause big starting issues, as well as affecting compression. If the crankcase can't hold pressure as the piston comes down, the cylinder may not fill completely when the ports open, which can directly affect your compression (making it hard to start). Something you might want to have a look at anyway.