When we do large odd shaped slab flattening my routine is to stand above the slab as high as I can get (step ladder if needed) and I take a photo from directly over the slab with a tape measure laying on the slab. I then import the photo into software and scale the photo to the tape measure. I then quickly vector around the shape of the slab and pocket from there.
We run a 5Z insert fly cutter that is just under 4" in diameter and I typically fire up the spindle and manually find the high spots on the slab with the pendant or keyboard jog. If its way off I may manually hog down some of the high spots until Im relatively close to hitting the whole surface and wont be cutting a bunch of air.
Then just setup a pocket tool path with no profile pass, raster, offsetting the vectors outwards by about 2/3 the cutter diameter. Cut depth/feed/speed will vary based on material.
Very little issue with insert tooling and tearout but if it is an issue we will just run a super light final pass. Large cutter running at 9K and a light/slow final pass and we come off pretty much at 120 grit.
I agree with BH. Big cutter from the start and you find a high spot and you'll stall the spindle and either send a servo off line or shove the part. I find though if I just chop the stepover a bit (we usually run 65% on spoil board) and drop the feed Im ok. Having the pendant is nice because I can set it to "feed" and using the jog wheel and my ear if the cutter is moving into a heavy cut I can dial back the feed on the fly. When out the other side I just bring it back up. If in air, dial it up to 200% until its back in the work.
We typically do the same with wedges as needed and I usually just box the slab in with scraps vacuumed down for the first side and vac down the second side or use scraps again if we cant hold it (holes/checks/whatever).
Watch for flying knots and loose chunks.