My Sixty-5 centerstand raises the rear wheel at least an inch off the ground. If a centerstand starts to settle, it would seem the CS frame mounts are deforming for some reason. Don't let anybody sit on the bike while on the CS.
As far as needing a free rear wheel for engine timing - I use the same method I used 45 years ago. I engage the kick start lever pawl by hand operation. Then I use a RUBBER mallet and gently tap the kickstart lever downward in tiny increments. With the spark plug out and using a plunger gauge there is little compression overthrow.
This can be done out in the middle of nowhere just using a piece of welding rod stuck down the spark plug opening and using a shoe as a KS lever tapper. Close enough to get one home - after being a good show for bystanders! Used to carry a marked piece of welding rod in the old days, but now I carry the nifty little plunger gauge in the tool kit.
Regards, Foggy