We've had a series of near-70 degree days here in the south SF Bay Area, and I had my first day off in a month, and the boat was sitting there in the back driveway. Some observations:
Raising a hinged mast single-handed isn't all that hard, although it sure does look tall at the point in the process where it's secured only by the hinge pins.
It's better if no one's looking when you rig the boat for the first time in a long time.
Trailered sailboats look a lot less forlorn when they've got the mast and shrouds up. Raise a sail for the first time in months, and it's "Oh, yeah! That's why I do this!"
The Fundamental Law of Important Objects in a Gravitational Field: If something can fall off the boat, it will.
The Law's corollary: It's better if this happens in the driveway than on the water.
Now to find some time, and some water...