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The following comments are from the perspective of a Goderich 35, a heavy displacement, cutter rigged, steel cruiser designed by Ted Brewer. The discussions around the pros and cons of the cutter rig note the difficulty of tacking the jib or genoa between the headstay and the staysail stay. This is indeed true. However, there are a few hints for the novice
Tacking a cutter is difficult only if you ignore what I believe is a fundamental rule: when going to windward, never try to tack the headsail without the staysail deployed. If you do, the headsail will want to pass between the mast and the staysail stay, hanging up on the latter, and in the process and usually necessitating sending someone forward to clear the sail with considerable effort. If the staysail is already deployed when tacking, the headsail overlap will slide forward along the windward face of the staysail and "round the corner" of the inner stay, slick as a whistle. Granted, when sailing shorthanded, it is still a busy moment handling the two sets of sheets and timing is everything. I prefer a staysail with little or no overlap and heavy enough to serve in heavy weather. When tacking, I leave the staysail sheeted but take up all of the sheet slack to windward. As the boat turns through the wind, the staysail remains backed, helping both the boat and the headsail around, and remains that way until I have re-sheeted the headsail for the other tack. I then release what is now the windward staysail sheet and set up the desired sheet tension on the leeward one. Now this process won't win you any points with the racing crowd, but in a short handed cruising situation, it gets the job done.
Of course, off the wind, or even on a very broad reach, the staysail is generally furled, as it starts to interfere with the head sail.
From a cruising perspective, I like the cutter rig as it facilitates shortening down sail as the weather picks up. While I use a roller reefing genoa in light air, I find that it seldom furls down to a well performing size for close hauled purposes. In this instance a large high cut jib like the "yankee" has the most versatility. In respect to the staysail, keep it as a fully sheeted, loose-footed headsail, rather than boomed and self tending as in many production boats. The former is much more efficient.
And last but not least, assuming you have an older style cruising hull configuration; when going to weather, don't try to pinch her up too close. Let her fall off a little, and build a little speed. Your cutter rig will perform much better, and you may be surprised at how much your gain in speed through the water will make up for a somewhat wider sailing angle.