Bass Bug....only for the sake of discussion...

That wrapping jig looks great...

But let's say we go all the way through like Kaboom...then I am visualizing a dowel with a bolt seated in it ...[however]...but the thread side down...then a wing nut under the board ... I don't think the board has to be turned over ...just position the peg and reach under and tighten the wing nut...no visualization necessary....in fact you could hold the wing nut and turn the peg.