I chose heavily reinforced, moderate weight sails for my sailboat. I converted the main from
furling (the old Hyde system) to fully battened with 3 reefing points. I went to a slightly lighter weight jib and it's done well in lighter airs. I bought heavy storm sails for the main (on a separate track), and a storm jib that I could zip over the existing jib. I also added a storm
anchor, some line for warps, and other storm
gear.
I'm a believer that UV can do more damage to sails than flogging. I make sure the UV cover for the jib covers the entire sail when furled. I also installed lazy jacks and use the
mainsail cover every time I
anchor.
I resisted the urge to buy used
racing sails deciding that dacron was the way to go. Dacron seems to last longer and that's what I was looking for. I also made sure my
sailmaker triple stitched the reinforcements, added chafe around the areas where the spreaders might rub on the sail, and made sure the slides moved easily and didn't twist the sails unnecessarily.
Since I sail solo most of the time and space aboard is at a premium, I've avoided the chutes/spinnakers/downwind sails in favor of wing and wing with a pole and preventers. Next time, I'd consider a slightly lighter main so that downwind the sail holds it shape a bit better, but so far (22,000) miles, the sails are getting a bit long in the tooth, a bit less efficient, but still usable.