Sails for a long trip
This season the winds below 5 degrees north were light and confused, but punctuated by heavy squalls. Some boats saw 45 knots in the squalls.  The sea state was in constant flux. Sometimes it was lighter than San Francisco Bay. Other times there were big swells from two directions.  I never saw waves coming from the same direction as the wind. At least not for more than an hour or two. The trip was often uncomfortable.  Sometimes making meals was impossible. I spent entire night watches literally wedged athwart-ships, staring at the stars, because the rolling was too violent to safely allow movement.
There are just 2 options to control rolling: change sails or change direction. We tried both, and often the result was a miracle. My advice is to plan ahead so that you have many sail options, and then to try lots of sail and course changes. Just when you are most uncomfortable and disinclined to “experiment”, that is when to get to work.
Sails give stability but there is a cost. For one, in light winds the sails add stability by absorbing the rolling energy as the mast tries to fly back and forth. This means wear on sails, ropes, and rigging. You may want to consider a new set of sails when you get back, not when you head out. Also when one of those 45 knot squalls comes along, you have to get to work really quickly. Some squalls are harmless, others are freight trains: a line of high wind that you can see approaching. At night, unable to see the line, you might have less than a minute of warning. Getting caught with your spinnaker up, as we did, can result in the loss of the spinnaker. Or if the sail is tough enough, the boat may lie down and take on water. I don’t want to think of what would happen to a catamaran in this situation. Several crews I talked with found that their light sails were blown out early in the trip, and they had to limp along with smaller tougher sails the rest of the way.
For people close to land, sailing is what happens between 5 and 25 knots of wind. Otherwise the engine takes us to the anchorage. Why would we wallow in less than 5 knots or take the brunt of a storm?  Our sail inventory will of course be optimized for these conditions. But before a trip far from land I suggest focusing on the extreme ends of the spectrum. Be able to reef quickly to tiny tiny sails. Be able to pole out giant light air sails. Have twin headsails. Consider a sacrificial mainsail that is high aspect and in poor shape for a riding sail. And because I don’t know what I am talking about, read the accounts of others. But read with a passion, for if you plan a long trip the rolling boat and need to shorten sail in squalls will define your life.
Consider the log of Sockdolager, a Dana 24, whose crossing from San Jose Del Cabo to Fatu Hiva took 38 days. Their comments ring true with my experience, even though I was on a 38 foot boat.