The cutter would give more options with smaller sail areas wouldn't it?
I think whatever I get, I'd like a self-tending headsail, or in the case of a cutter a staysail with a jib-boom. I think the staysail on a cutter can be equipped that way without interfering with anything, couldn't it? And then use a 100% yankee on the foresail so it won't get fouled on the inner forestay when tacking.
And then of course, I'd have to look at an autopilot or air vane to allow me to leave the helm occasionally...