Stepping your own mast on a smaller boat is often done, especially if there is hinged tabernacle. Been there done that and then had the yard step the mast with a gin pole. Unless the cost is exhobitant, it is faster and safer for the crew and the boat to use a gin pole. If you lose the mast, it is likely the step and tabernacle will be damaged along with wherever it lands.
What kind of winch is that? It looks like it is made of plastic.
I also suspect the fully rigged 28' mast weighs somewhat more than 50 lbs, that would be less than 2 lbs a foot.