In many ways, for the kind of sailing that most of us do, the cutter rig is the worst of all worlds. At the heart of it, it is the hardest rig of the single mast rigs to shift gears. Beyond that it requires the most complex rigging layout. Proportioned to actually act as a cutter rig, it is the least efficient sail plan meaning that you need to carry a lot more sail area in order to achieve the same drive as a fractionally rigged sloop, and that increased sail area means more work to sail and more hardware, and a lot more cost to maintain.
To be frank, at least here on the US east coast, most of us spend the majority of our time sailing in a wind range between 8 to 20. The kinds of gear shifting that we end up doing is a far finer tuning than a cutter rig is easily capable of. The intermediate stay and the proportions of the headsails to mainsail make a very limited gear shifting capacity, for the most part, with shortening sail the primary viable option at the upper end of the range.
But my biggest gripe with Cutters has to do with the way boats behaive as the wind nears the upper end of its standing sail plan's wind range. Most boats develop weather helm as windspeeds increase due to a variety of factors, heeling, sail stretch and rig sag being some big factors. At the upper end of the windrange, you end up having to reduce sail rather than depower as you would with a fractional rig. The standard regime is to reduce headsail size or completely furl the headstaysail (Genoa or yankee), but because the headstay sail is so far forward, that simply adds to the weather helm, which means that you need to reduce mainsail area as well. In other words, as typically configured, cutter rigs lack the smaller incremental stages typically associated with more modern rigs.
Respectfully,
Jeff