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I've never sailed a cutter, but I would think the following problems might occur:
* Headsail getting fouled on inner stay when tacking.
* More lines to make a mess in the cockpit
* That jib-boom would be a tripping hazard
* Not enough open foredeck space for a dinghy
Other than that, I would think that it's a pretty versatile and easily-managed sailplan.
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