Cut the keyhole and test fit the gimbal tonight. Was really happy with how it turned out. The transom ended up exactly 2" thick all the way around. Maybe plus or minus a 1/32", but it turned out great in that regard. Few pictures of the process.
To cut the angled holes I actually used 3 drill bits. I had a shallow hole saw with a long shank to get the pilot hole going and one of the sides started started. Then used a deep hole saw to cut the rest. I also used a paddle bit throughout it to drill flush with the transom to remove material so the hole saw could keep going.
Shallow starter bit:
I'd have to remove material to keep the angle going.
The 2 angled holes are cut, and now I'm cutting the keyhole. The blue tape sort of helped keep the scratches down but not as I had hoped. The relief holes at each turn worked out and gave me practice before drilling the bolt holes.