that chain is at the point it should be cutting like mad.
However, you’ve lost the hook. Big time. By the time you get it back, the chain will be nearly done. Done properly, you can file a chain until all you have left is a triangle when viewing the cutters from the top. At this point it COULD be cutting its best. Easier said than done.
Once the cutters are about 1/2 gone, step down to a slightly smaller file (13/64). This will help to keep your gullet correct. Your chain has NO gullet..
THIS IS IMPORTANT: you should never really have to push on your saw. Ignore the you tube clowns levering on those ridiculous big dawgs (they have a place, but not in what your cutting pics showed). That’s not how a sharp chain needs to be run. The saw should self-feed to the point you should almost have to hold it back/throttle it back a bit when doing precise cuts (like approaching the dirt or the hinge in a back cut). This self-feeding was already mentioned, but I thought I’d throw that out there again.
Your compression tester appears to be working, as long as you have a working decomp, that is.
Perhaps the saw was never broke in properly to get a good ring seal..? It happens.
If it were mine, I would file that chain correctly and let the saw eat at its own pace in some 16-20” wood. Over and over again. I would advise you to buy a new chain, imprint the gullet shape in your brain, add a wee bit of sea foam to your gas tank (to clean up the carbon in the ring-lands).
You’re young and strong, stop using the decomp. Damn things leak all the time..
That saw would be happier with a 24” bar full comp chain. Smoother, faster.
Try to post the requested video with the saw working (after you get your chain in order).
You will be a competent filer soon.
50cc 16-18”
60cc 18-20”
70cc 18-24”
Pretty standard bar sizing except in BC, Canada and most of the US, it seems.
Anyway, you have some good saws. You’ll get it sorted.
That 372 WILL NOT pull any bar through anything with that chain. No saw will. Notice I said “pull”, not push.