Big bore Stihl 066 pistons are plentiful aftermarket, so I’m not sure what you meant in your post “reallllly hoping to find a 660 56mm piston so I can use big bores and actually machine a bit more (w/o freeporting....on that note”.
Never tried using an aftermarket Stihl 056 56mm in an 066 big bore cylinder...the WPs are different diameters. But I’d be more leary of the compression deck heights being way different, as the crusty guy in the linked video never mentioned that part.
He also never mentioned the fact that the small end rod widths differ, so going your route may end up running the Stihl 056 wrist pin needle bearing tips unsupported and also allows the 066 con rod a lot of side-to-side play up top, not good if the 066 saw is a “rod centered” design. The 056M uses a 14.5mm wide bearing, the 066 is only 13mm.
As far as your free port versus squish compromise question, I’d adjust the free port to zero & just accept the 0.027” squish. For a 100cc saw, that squish will help keep the starter assembly in one piece!