So if I end up going the cool head route cause I'm not too confident my head will ever make its way back to me, what's a good cc dome size to go with? Also could I run one dome for drag racing and swap it out for another dome for trail riding? O ringing a cool head about how much does that cost and has anyone ever o ringed their cylinder?

Why to you want to screw up your engine design by using the right head one day and the wrong head another day.   

It is the total engine design: ports, pipe, reeds, carb head and ignition timing that determines what octane fuel your engine needs.

Just changing the compression ratio does not have a large influence on the octane rating that your engine needs unless you reduce the compression to the point that it makes power like a 250.  If you reduce your compression ratio this much, your pipe and ports will be a mile out of tune with each other. 

Most of this stuff about using different heads or domes so that you can have a engine that can run on any fuel began when the billett heads were first started.  I am not sure if was a marketing campaign to sell you more domes after you bought a billet shell or if it was absolute ignorance about the intricate design and understanding of high performance two strokes on the part of the billet head industry.