Raise and lower the mast ON THE TRAILER. Don't try to do it in the water. Dropping the mast is fairly easy if you have 2 people . . . one person in the boat behind the mast, the other unhooks the jib at the stem fitting and starts easing it down until the other can take it and guide it down. Once it's down, unhook it from the tabernacle, unhook the shrouds from the boat, and put it on the mast crutch(es). Tie up the shrouds with ball bungies.
If you're alone it gets a bit trickier. Easiest way is probably to rig a line around the trailer post and tie one end off to the jib furler and cleat the other to one of the jib cleats with plenty of free line . Release the jib pin and go back to the cockpit. Ease the line and the mast should come down so you can control it.
Set up is just the reverse - The sails both went in the bag until I was ready to raise the mast. Hook up the shrouds, hook up the jib, and
up it goes. The on with the boom and sail and go have fun!
Does your trailer have a mast carrier at the front like the one in this picture?
I had a canvas cover so I unhooked the shrouds and bungied them to the mast. I also made a support for the stern that used the rudder gudgeons and supported the aft end of the mast. As you can see from the photo below, there was a bungie holding the mast crutch down and a strap holding the mast to the boat. The rope going through the scuppers has a loop in each end for the hooks on the strap.
Let's see, other advice . . . don't fall off the boat while it's on the trailer.
I did that, luckily I was able to tuck & roll so I didn't get more than bruises.
Once you get the hang of the boat, raise the board when you're heading downwind, just don't forget to put it back down before you head back upwind.
If you want to go out in big wind, send the sail to Ullman San Diego for reef points.
Lots of people put pool noodle foam in the mast to keep it from filling with water and turtling if you get knocked down. A hobie float is even better.
I put a boarding ladder on the stern of mine. It was only 2 steps, so hard for the Admiral to get back in. If I did it again I'd probably get a 3 step telescoping one.
We mounted a car trunk cargo net in the cuddy and we used to have a cooler that just fit through the hatch. I also kept a canoe paddle up there and a couple of throwable cushions.
Note the fading on the jib in the first photo. If you're going to moor the boat then invest in a jib cover. My wife made a set of covers from a Sailrite kit.