Mathew, if you do put the box in 1st, the method I have used is to put masking tape on the box so it overlaps the slot by about 2 mm all round, then set the box in the board with resin and chopped glass and let dry. Then glass over the top and before the glass sets (whilst green) get a very sharp stanely knife and cut out the glass where the slot is, only cutting on the down stroke. This worked quite OK for me but I agree you may not be able to tell if it comes loose. I also used wood reinforcement so I doubt if the box would ever come loose, probably rip the back of the board off

Yes I made a speed board about the same time you did. Used V all the way through and double concaves just fading out before a flat section in the tail. It went OK but never used it in ideal conditions with a decent sail. What design are you using ? I have considered reshaping mine as well.