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it the past given the effort vs expense of replacing the top end...
I have always replaced the small end bearings, pins, rings and pistons at the same time. Now that original pistons arent at hand need to reconsider pistons every second ringing.
I got new ring sets from Cradleys last month - I am not sure what stocks are left (being you can't get the OEM pistons) - genuine
head gasket and base gaskets are still available.
Remember it not just the piston and ring that wears out
You may find you might scratch a new pin fitting into an old piston - not sure what other people recommend here - certainly if you do go for new bearing get a new pin as well.
If you do fit new pins (doing bearings), you could, on the safe side (protect and) chill the pin, warm the piston to get the loosest/biggest fit (dont just push them together old with new at room temperature) at time of assembly
Can't really tell from the photos what ridge surface is left on the piston (theres still appears to be some teflon on the skirt?) so probably okay. I bet most people never measure the piston and bore (clearance) or ring - so thats up to your discretion on how worn they are - given you dont have first hand (previous) assembly history on the motor. You wouldnt take the motor apart measure the ring gap find it in within tolerance and put it back together with the old parts again - pointless
Refittig the barrel, very loosely and rotate crank through several strokes, then stroke the crank midway and fasten down - you're trying to get the cylinder bore the most concentric with the piston here. MY OPINION is you will only achieve
half the accuracy if you follow some peoples advice on both barrels and head as one unit. You are aligning multiple parts to ONE plane of reference - NOT trying to conform multiple planes/axis to one reference (a warp in the head will create cylinder axes that are non-parallel to the rods and non perpendicular to the crank/smallend) and then try to bend them back into line by bolting them to the crankcase?? -
a bit like digging a tunnel from two separate ends they never will meet exactly - therefore is not completely as straight as it could have been starting at one end going straight through.
You should polish the combustion chamber surface with wet and dry - or even just Autosol and patience - to get a mirror finish !!
Consider your riding style and what oil you are using and if youre only pootling around a hotter plug - (the piston crown seems quite clean but the chambers not so well

)
A two stroke roadie that gets treated too gently (laboured and never reved out) wont run clean (liquid oil buildup in pipes and eventually pistons) - if for no other reason bomb the tin-boxes with giant plumes of KR smoke
Minimum course of action (cheapest)... new rings (old pistons), and genuine gaskets