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If "rig" means more than just your truck and trailer.
Mast-Raising Systems
Trailerable sailboat owners need help getting that stick up in the air. Have a system; if your boat didn't come with some method of "easy" mast raising, copy off one that did. Using the trailer winch or installed hardware to create a fulcrum for leverage is better than five friends and a lot of sweat. Keep in mind that you have to take it down at some point, so consider that in your scheme. Once you have your method, practice makes perfect. Label the components and their order of use if you have to. Remember the grade you're on (hills) can significantly help or hurt your efforts, so experiment a bit.
— John Adey
Less Stick On The Stick
Do you use duct tape to secure the rigging when trailering your sailboat? If so, buy yourself a roll of cheap kitchen garbage bags. Wrap the mast and stays with an unopened bag first, then tape tightly as normal, but over the bag. Snipping the tape and bag together will leave no adhesive on the spar or wire.
— Don Casey
Automatic Topping-Lift Adjustment
When you're off the wind, does your topping lift slap and chafe the leech of the mainsail? If your topping lift is adjustable, you can tighten it, but you'll need to remember to loosen it again as the wind moves forward and you bring in the sail. An easier solution is to whip the ends of a length of stretched, light bungee cord to the topping-lift line. This keeps the topping lift under tension even as the boom rises, with the loop of line forming between the whipping typically remaining clear of the sail. To reduce the size of the loop, add a couple of intermediate whippings.
— Don Casey
Stepping The Mast
Let's face it, rigging is a mess when the mast is down on deck ready for transport. I use Velcro wraps to keep the rigging together then bungee the slack to a nearby cleat or other attachment point to keep the shrouds and stays from flapping against boat parts and causing marking or damage. Just make sure the bungee isn't so tight it causes a kink in your wire. Putting a piece of rubber chafing gear on the bundle to limit the bend before you hook the bungee cord is a good idea. Leaving stays attached to their chainplates saves you tons of time at the ramp.
— John Adey
Help The Crew By Color-Coding
To avoid hassles out on the water, color-code your lines so they're easily identifiable to your crew. Examples of colors to use are: mainsail sheet & halyard — white; jib/genoa — blue; spinnaker — red and green for guys; vangs & travelers — black.
— BoatUS Editors