As Cam mentioned, sea and air draft could be issues. That is where Cam's old boat, the ketch rigged 52, had an advantage. Along the lines of what Jeff said above, there comes a point where it begins to make sense to split the rig. Where exactly that point falls is debatable, but I think once you're up above 50 feet you're well within the realm.
I could be mistaken, but I seem to recall that there is a schooner-rigged version of this model? Maybe that would serve?
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT