What was the compression to begin with, before the damage occurred and was the fuel fresh? Trailer running doesn't generate much heat or cylinder pressure, also low throttle positions mean there's not much oil being delivered unless you added oil to the fuel (I've never seen too much oil hurt a 2-stroke and it's easy to add oil to the fuel tank. Assuming the carbs aren't dry, the oil is carried along with the fuel). Too much oil will foul plugs, I still recall the days we ran 10:1 non-detergent SAE-30 in our egg beaters, LOL.
Detonation from ignition timing advanced too much, stale low quality fuel, too lean A/F mixture will eat holes in the piston crowns. I'd guess the previous engine suffered the same fate for likely the same reason?
General 2-Stroke rules: If bore is too large for piston diameter heat can't transfer from piston crown through the thin oil film into cylinder walls, piston overheats as a result, heat destroys oil film and piston melts. Overheated pistons can cause detonation IMHO, some will argue that but I believe if the piston is hot enough pre-ignition can occur (which isn't the same thing as detonation, see link). Regardless, detonation occurs when the fuel stops burning prematurely (for whatever reason) as if when there isn't enough fuel in the mixture or it flashes from being poor quality or stale fuel.
I'd say most 2-stroke premature engine failures are a result of carburetor and other fuel system issues.
Never ever break in an engine with no load, the rings usually won't seat correctly and the 1st 10 or so minutes are the most critical for ring sealing.
I don't see chamfer around those ports, are the rings broken from snagging on the sharp edges of the ports? See the scoring above and beneath the port indicating oil was wiped off the rings as they passed the sharp edge of the port. Chamferring if done correctly leaves oil film on the face contact of the ring and scoring above/beneath the ports indicates lack of oil due to being wiped away (or possibly incorrectly gaped ring ends).
See this article, I don't recall if he speaks directly for 2-strokes but more so high-strung ICE:
Engine Basics: Detonation and Pre-Ignition by Allen W. Cline