Have to at least pull the cylinder off to see how bad the damage is. If the piston is scored up (by the sound of it) pull it off the rod and check for ANY up and down play on the rod and for any rough feeling crank bearings. If the rod has any up and down movement or noise/rough feeling as you roll the rod around,the engine has to be split, a new rod kit pressed on along with boring out the cylinder and a new over size piston. Just my two cents,I learned the hard way on just doing top ends when a couple machines came back that I thought the bottom ends were ok. If the bottom end goes out,usually it will take a new top end with it. Just extra cost when cutting corners on two strokes,especially old ones that you just got a hold of.

 

I pulled the head off and the piston top looks fine. Light coating of oil on everything. It moves up and down when I use the pull start. Not sure if I maybe did the compression test wrong but it still didnt blow my finger off the spark plug hole. Should I put everything back together and check again or should I pull the rest of the top end off?

 

You can't reuse the old head gasket and you can't tell if one side of the piston is seized/scored up unless you pull the carb and the intake manifold and exhaust manifold. Better to just tear it down and see what you have.Whether the compression reading was accurate or not,it should have enough compression to blow your finger off the spark plug hole.

 

Finally had some time to tear this whole thing apart. The gasket from the head to the jug seems to be metal and cant be reused? The gasket from the jug to the bottom is what I would call normal gasket material. The gasket from the head to the bottom was missing part of it when I got the jug off. The cylinder looks fine and so does the piston. No play in the rod and no noise when I move everything around. Should I try just replacing the gasket or say screw it and replace the entire top end?

 

The metal head gasket MUST be replaced along with the fiber coated base gasket. You can do a rough piston to cylinder clearance measurement with a feeler gauge. Remove the rings,place the piston in the bottom of the cylinder as it normally goes,hold the piston skirt even with the cylinder skirt and see how big of a feeler gauge you can get on the opposite side of the piston skirt. If .005 or larger on a feeler gauge,I'd have it bored out to the next oversize that would clean the cylinder up.Plus always check for ANY up and down play on the rod! Even if you notice a small amount of play, the rod has to be replaced,then you might as well replace the crank bearings and seals since you're already there.If in doubt take the piston and cylinder to a machine shop or dealer. You're dealing with thousandths of an inch clearance tolerances that a lot of people don't realize how critical it is that every thing's right or it can be money down the drain if it's not. Plus can't see your pic..