Maybe something wrong with the rings , i would take them off the piston and sit them on a flat surface to make sure they are not warped / twisted . Then i would roll each ring around the groove in the piston to make sure there are no tight spots , you can check the ring groove depth clearance at the same time . When you checked the ring gap how hard was it to get the ring into the cylinder ? Did it feel like there may be an abnormally high amount of ring tension ? Is there a small amount of clearance between the walls of the ring groove and the ring ? (I would be aiming for 0.003 – 0.005 inch or so) I would then look for any taper in the ring and piston groove – to check the ring just give it a light lap on a flat surface ( surface plate if you have one ) with some fine wet and dry paper ( do both sides ) , look for any high spots or burrs and to check the groove in the piston use feeler gauges or a gauge block if you have a set . Lastly , in the ring groove is the a small radius where the sides meet the bottom of the groove ? If so check the inside dia of the ring to see if it has a small champfer to accont for this .
In the 30+ years i have been building full sized engines i have seen some weird things – a piston ring that was thicker one side than the other was an especially memorable event that had me scratching my head wondering why the piston was so difficult to get into the bore , once i stripped it all apart and rolled the ring around the piston ring groove i discovered the tight spot . Fortunately that was only a mower engine so the supplier excanged them for a different set .
Just to add to what Jason mentioned with cylinder finish , you can wrap some fine wet and dry paper around your hone and give the bore a finer finish ( don't polish it ) just a few stokes back and forth to knock the tips off the honing marks and you can also give the outside dia of the rings a light hit with some fine wet and dry if the finish is a little rough – once again don't polish too much as the fine scratches help the rings to bed in .