At least you are located in a place with many options and many people able to perform such work. In out of the way places it's not so easy to even think about such things. Organization to minimize haul out
time would be an issue in Annapolis
. You pay a lot by the day just sitting around waiting.
I would take the time to examine internal wiring
of the mast as well as long as it's out. This should not be a regular exercise.