The biggest challenge I've found is hoisting and dousing sails single-handed. It's not much of problem when at the mooring and the boat naturally heads into the wind.

But for other hoisting/dousing situations I appreciate:

- a reliable motor and autopilot to point upwind
- hanked headsails - no foil
- boomkicker as topping lift for boom

One mainsail is equipped with slugs on the luff so it's easy for a person to hoist without having to feed boltrope into track. Dousing is also easier - and safer in a stiff breeze - as the luff stays attached to the mast (like hanks on the jib).