My father and I owned a cutter for roughly 11 years before moving on to more modern rigs. The cutter was fine if there was enough wind to get by with just a forestaysail and Jib. If it was too light and we had to use the genoa the boat was a real pain in the butt to singlehand as the genoa hangs up on the forestay and so meant a lot of winching under load and a really slow tack. I have also been asked to sail on a small IP to help them figure out how to tack the genoa through the headstay without stopping the boat and found that the only reliable way was to partially roll in the genoa on its furler. then tack and release the retractor. Again, not my idea of an ideal single-handing rig. The other thing that I found with cutters is that the staysail usually does not have enough area to properly balance the mainsail producing tremendous weather helm. This can be offset by reefing the mainsail in which case there was not enough sail area to drive the boat through a chop. The cutters that I have sailed generally have needed running backstays in heavy going when sailing under just staysail and reefed mainsail, which again is not my idea of an ideal singlehanding rig. (Also unlike most fractional rigs with runners, the runners on a cutter generally hit the mast well below the head of the reefed mainsail resulting in a boat that is no longer self, tacking even when reefed.)
While a lot of folks swear by cutter rigs for offshore sailing, having owned and sailed both for many years, I strongly prefer the smaller headsails, greater simplicity of a fractional rig and wider wind ranges permitted by the ease of depowering a fractional rig which reduces the need to reef or douse a sail. To me for boats under perhaps 40-45 feet a fractional rig is much better for single-handed cruising either on or offshore.