Okay, so I'm looking at the intake ports of the cylinder and curious to see the exhaust port next! (photo please if you have a chance).
Also wondering if the machinist dressed the opening edges around the ports by chamfering them with a die grinder and carbide burr or maybe round file device so the rings aren't prone to snagging on the edges of the ports?
Do the edges feel sharp to your fingers?
The overbore should include this step of preparing the ports and sometimes it's necessary to disassemble after the first heat cycle and repeat the process of chamfering if vertical stripes are found.
http://www.ccspecialtytool.com/2-stroke-porting-and-polishing-tips-tj