Typically what I find on saws with lower compression that do not have scored pistons/cylinders are worn rings, rings with loss of spring tension, piston ring groove wear, piston surfaces worn smooth (no oil retention, decreased seal at low rpm), carbon in piston ring grooves causing stuck rings.
Honestly the ms-290/311/390/029/039 are a pain in the azz requiring lots of time for full disassembly of the saw to change the piston/cylinder, the sealant must be applied not to thick or too thin and the crank seals hand held in place when tightening the bolts down. The cylinder base bolt hole threads have to be cut by the bolts and are best to be done before assembly with a good chance of a reused bolt breaking off. When built with oem parts and treated right they run forever.