Like others have said the tape doesn't slip, however it also doesn't stop. A wood pattern would help keep you aligned, and could be tall enough to be a stop, but I think it would limit the overall size of the board to whatever sized layout you made. Something that was nimble and moveable would probably take up more time, than just watching for the tape to start sweeping shavings.

For something already made, possibly chuck up one of the "VIX" type bits, that had a large enough drill to suffice for the size of your peg hole. They definitely can limit depth, are pretty cheap, and can be had in 1/4" drive, or a straight shaft that could be chucked in most anything, or at least into a device that could be.

Adapter for brace to hold 1/4" shanked bit

Vix bits to 1/4"  If the pins are 1/8" maybe something 9/64 would work?