Re: Singlehanding a 41' Hunter DS?
I am 65 and single hand my 44 footer for about 6 months of the year between Trinidad and St Maarten. I see no problems in what you plan to do with two caveats.
1 - you need a bowthruster to help you dock..
2 - if you are going to be in a marina in Florida in the summer you need some serious AC.