Yes - I used the trailer winch, with the boat still fastened to the trailer, when I had a 16 - that's a real good one if you trailer, but it really takes two people...
But a few years after we moved across A1A from the beach, so we could leave the mast up, my wife had some skin cancer removed, (I burned her out sailing too much...) so I got the 14 for solo, and left it on the beach - no trailer. That's when I figured out how to step the mast solo.
I think it would be harder with a 16, unless you're very tall and strong, or have another person - LOL.
NOW - I have a
Bravo*, which I'm dying to try - I'm waiting for some fairly dry, warm, and low wind conditions for the first sail.
It's been raining a lot here, and winds 15 to 20 mph, which would be no problem, if I knew the boat, but I want the first sail to be easy and fun...
Tomorrow or Sunday looks like it might be good -
* The condos that slowly built up on "my" beach, finally forced me off. My 14 "blocked thier view", so I sold it to a guy that manages a condo down the beach. He says he'll let me sail her again. I keep the Bravo on a dolly at my house across the street.