EJ,
Regarding the cribbage board, I believe I might be able to help you in that regard. I use my SO3 to make and sell cribbage boards on Etsy, and I have drilled tens of thousands of holes by now with carbide drill bits from drillman1 on ebay. I use 0.1250" drill bits for my standard sized boards and 0.0781" drill bits for my portable sized boards.
The 0.1250" drill bits are made for drilling holes in PC boards, but they do a great job cutting bamboo, wenge, cherry, padauk, zebrawood, leopardwood, beech, maple, oak, katalox and chakte viga. I usually run them around 15K rpm and make 0.050" pecks down to 0.450" for each hole. Each bit usually lasts 10-12 4 player boards.
For my smaller boards, I use the carbide 0.0781" bits also from drillman1, and they work just as well, and last about as long as the larger bits. I also use the 0.050" peck distance for them as well.
I design and lay out all my boards in Inkscape, and use makercam . com for creating the g-code.
I use end mills down to 0.0150" for engraving the boards, so don’t be afraid of going small with your bits.
I don’t have any good pictures online of the 0.1250" holes, but here is an album with close-ups of the 0.0781" holes. The engraving of the lines and numbers were done with an 0.0150" end mill.
Let me know if you have any questions, and I’ll see what I can do to help.