The most cylinder wear occurs at TDC. If we carefully measure a very worn engine (older engines were prone to this) we might find 0.0005 inches (near nil) of cylinder wear at the very bottom of the bore, where rings don't touch, and 0.020 inches at the top ring position. (or more) . This creates a cylinder ridge so deep, it becomes difficult to remove the piston as the rings catch on the ridge. Hence the need for a "ridge reamer" to get the pistons out.
Just a guess, but possibly your cylinder has a slight ridge, under which is enough wear to prevent good sealing, or the ridge itself touches the top ring and pushes on it a little, causing a loss of seal.
But that's just a guess. It may have nothing to do with wear, and everything to do with how the rings sit in the ring-lands.
In aircraft, we use a differential compression tool that does much the same thing as you are doing. We often have to move the prop a bit back and forth, to get the rings to seal up.
Start at about the 20 to 1:30 second mark to see him move the prop to get a good seal.