Homemade mast raising system
If you search this and other trailer-sailor sites you'll find a lot of people use gin poles. These are set at right angles to the mast, a few feet up from the base. I use an aluminum pole, about 7' long. On one end is a crutch that straddles the mast. On the other is a wooden block with an eye strap on one side and a turning block on the other. These are opposite one another. Midway down the pole I have bolted on a light-duty trailer winch (looks like a big fishing pole). The jib halyard is attached to the eye strap and cleated taut; and some braided line extends from the winch, to the end of the pole, through the block, and then attaches to the bow pulpit. I have a telescoping mast crutch, mounted in the rudder gudgeons. I bring the mast aft and secure the base to the tabernacle. The gin pole gives a good angle of pull on the halyard, with a sufficient "upward" component. The mast needs to be secured from side-to-side motion while in transit, at least until the aft lower shrouds kick in. For this I use "baby stays" (or "baby shrouds", more properly). These are attached to tangs on the sides of the mast, 7' up from the cabin trunk, and then to the top of the cabin trunk about 18" outboard from the tabernacle. These share the pivot point of the mast going up, unlike the shrouds themselves which are secured to the deck. For this reason they remain taut all the way up, or down, and provide some lateral stability. I made mine out of 3/16" marine braided wire and have attached them to pop-off couplings on deck, obtained from Catalina Direct. (They are a component of that $350 system they sell). With all this gear, I can comfortably raise & lower the mast single-handed, and can do so while afloat if needed (low bridge, big storm, etc.)The attached link is a picture of the winch set-up that I pirated when making mine.Hope this helps