Great post. You are truly a very knowledgeable person when it comes to 2-strokes. I played around with one of my pilot motors and calculated out some of the stuff you are doing, but never got too worried about ring pressures or clearances (I was using a wiseco piston and clearanced it to .0045" and never had an issue). I was able to calculate the CCR on mine and with the static compression at 165, I was able to keep the CCR low enough to run pump gas using a cool head and 47cc dome from K-fab. Beyond that though, I never got too far into engine modifications since I don't have the money, tools, or knowledge I needed to play around too much. Maybe I lucked out with the last pilot motor I built, but it sure ran strong.
Keep it coming! Even though I am working on transplanting an 07 phazer engine into my pilot now, I have a couple of chainsaws, and a weedeater to play with
To answer your question about which of your engines will need a higher octane I will "guess" engine #1. I base this on the fact that squish is so much tighter with a smaller profile towards the edge of the piston, making the likelihood of detonation much higher with lower octane fuel even though head #2 has a smaller chamber volume and higher CR.