Okay I'll say it: I enjoy changing headsails. And I will qualify: to a degree.
We have an array of hank-on jibs
. We do mostly daysailing, and generally use the sail best suited to the strongest wind we expect to encounter. If the wind is a bit lighter, it's no big deal.
On multiday trips in summer, we often have light wind in the morning which builds in the afternoon and then dies out completely in the evening. On such days we will typically switch jibs
twice. If we're going downwind, we will fly one of our symmetrical spinnakers
, again, because we like doing it.
Our vee-berth has two spinnakers
, three genoas, and a mainsail in it :P
That said, our next boat will have a roller furling
jib. We are pretty excited about the cutter rig
, partially because of the sail options, but also because I have this image in my head of motoring out past the breakwater without having thought about what headsail to use today, deciding based on conditions, and then, without getting out of the cockpit, pulling on a rope until I get what I want. I have a similar image for when the day is done and it's time to douse. Oh and, partially because of how sexy cutters (true cutters) are
Ideally our forestay would have a boom with a reefable staysail bent on.
Relatedly, there's lots of good ideas on this forum about tacking a double-headed sailboat, btw. You're always doing some work to tack a boat, unless you have a self-tending headsail; and many seaworthy cutters do indeed have self-tending staysails. In conditions where you'd have the jib up, "difficulty tacking" is not really an issue, and if you're in heavy conditions, a self-tending storm staysail sounds like a nice option.