Shindaiwa 488 wont start

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Hard to tell, sometimes the scoring can cause resistance which imitates compression.
It pulls over easily with the spark plug removed, if that means anything. Or it could be like you said a little compression results in alot of scoring resistance.
 
I put the new plug in now i'm not getting any spark at all. This saw is a mystery...
 
Fixed the spark issue by cleaning a bunch of mud behind the coil and flywheel. Will replace the piston and rings next. View attachment 928096
You need to evaluate the condition of the cylinder before proceeding or else you are just throwing money down the toilet.

You also need to figure out what caused the damage to begin with. The initial photos look like it may have eaten something that didn't agree with it... Like a piece of bearing cage. Post some good photos of both sides of the piston and the inside of the jug.
 

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