sorry if a bit incoherent, phone and other distractions are competing
honda only offers the .25mm and .50mm oversize pistons, when you go beyond that wiesco is the only option i think their largest is .80" over (inches not mm)
hoser and i differ on some of our methods, hoser does it the right way and i do it the slug way, yes a 20psi drop does means something but you don't have much time at all on that
Engine and there shouldn't be a problem or the last time.
it could be as easy as a stuck ring, bad bore/ hone, improper assembly or a multitude of things. its hard to tell if a crank or mains are going, but after putting three top ends on that you know about I would be suspect of the lower end. any crank play up and down is bad, a little side to side is ok, mains and seals are worth doing and absolutely use honda bearings and seals. I would do it all except the crank (unless its questionable) It be a shame to put a brand new ported jug on a bottom end that may KABOOM and mess it all up or at least lose a couple of bores over $100. in bearings and seals and a $400. tear down / assembling labor charge.
I ride a lot, i mean alot, 40+ weekends a year is not uncommon for me.
For years I rarely if ever do compression tests on any of my two strokes and i get great service life, 100 hours + and even more time on my two stroke bikes I race, all without a compression test, point is when an Engine is assembled and run the right way it will keep running with little to no maintenance. I try to clean my air filter and change my trans oil (dirt bike) every ride, other than that good fuel and oil mixed about 40:1 and gentle warm ups without prolonged idling is my master plan and it works.
There are either other problems causing this (carb/jetting, air leak, poor air filter seal/ maintenance) or the Engine is not being set up right, plain and simple.