saw porting
Did you end up chamfering the port edges? You really need to do that if you expect your rings to last.
Make a port map before and after every port job to find out where everything needs to be moved to.
For port width: measure the bore diameter. Multiply that by .67 (67% is a safe bet. You can go up to 70%, but then your rings will start wearing out faster).
Put a piece of paper in the bore over your port and rub a dull pencil over it to get a rubbing of the port shape. When you lay out that piece of paper, your port can be as wide as the calculation you did above (unless your piston skirt is smaller than that number or your ring ends fall within that zone).
I always widen the exhaust to 67% of the bore, then measure the area of the smallest point in the carb and make the intake the same area (widen it to that point, and make sure your piston skirt doesn't fit into the port).
I usually raise the exhaust and lower the intake if I'm looking for crazy high RPMs (I like working on mopeds and small motorcycles), but on a chainsaw, DON'T raise or lower ports. You want all the torque you can get. Raising and lowering ports will shift the power band up and kill the torque.
If you sheared the woodruff key, there are a few reasons that might have happened.
1) You didn't tighten the flywheel enough. I hope that was the reason.
2) You snagged and probably broke a ring in your larger ports.
3) You dialed the jetting in wrong and you seized the piston in the cylinder.
If you lowered the exhaust at all, check to make sure that the ring isn't showing in the exhaust port at BDC, if it is, throw out the cylinder. Don't run it. If the ring isn't in contact with the cylinder wall at BDC, it won't be able to cool off and will expand enough to seize in the bore after a few minutes running.
Thats just speaking from experience. Take it with a grain of salt. If you think it should run, try it out. If you're worried you went too far, it'll be better to buy a new cylinder than a whole new saw.
Eric