I don't think there's any doubt about how to properly measure mast rake...but on the beach, in between days of the regatta, I'm not to keen on grabbing a trap handle on a competitor's boat with a measuring tape in hand! However, when 10 of 12 class boats all have their shrouds in the last hole and I can't get close, it makes me wonder what rigging on my boat is different.

Are you talking about making your forestay loose for de-rigging or for tuning? Obviously if you loosen one shroud and not the other, your mast will be leaning (ever so slightly) to the shorter side which would be fine for de-rigging the boat but not so much for sailng. Assuming the shrouds are the same length.

Yeah- boy, how did we get here on this thread?