Need to find somewhere that takes winter liveaboards
I think that the climate conditions in Kingston are doable and it is a lovely place to live, but you need to have a marina that operates in the winter and I doubt that either of the two large ones in Kingston do (downtown and Collins Bay). I know of several marinas in Toronto that have significant winter populations (Bluffers, west side of main harbour (forget the name) and Port Credit). Now is a good time to check on availability since the one downtown at least has a waiting list.
In South Africa doing lots of boat stuff. Departure north from Cape Town around December 15th. Arrival in the Caribbean around the beginning of February, after 5300 miles or so.