Sorry; just got into this discussion late.

We keep about thirty-five boats on trailers behind the sand dunes at our local sailing Fleet Club (wnycatamaran.org - presently redesigning our website)and we have our own Kubota tractor for moving the boats from the parking area down to the beach. Some of the larger boats (Hobie 18s and up) are towed with their sails up (always into the wind or a close reach) and backed into the water, then slid off. I sail single-handed and this makes launching effortless. We have a series of pins in the water that you can moor your boat to while you take the trailer to beach and disconnect it so another person can use the club tractor. Many of us trailer to regattas, and no matter what you do, you will get water into a "watertight" cat box, so it is best to have ventilation holes built into it. You'll find that damp sails from a misty day on the water will dry fairly quickly on their own.

As always, before you put the sails away at the end of the season, make sure they are perfectly dry before you put them in dry storage.

You can make a good catbox for less than $125 by buying sewer pipe and caps. Look at different threads on this site because it's been discussed numerous times.

Wyatt, Fleet 119