"2 months for a weather window to cross over to the Bahamas isn't realistic."
Well I have another friend in a 44 foot sailing cat, seasonally moored outside Pascal at Dinner Key, who never made it to the BEEHOMS two winters ago. They just did not see a big enough weather window, or reduced wave height/adequate wind speed and direction, for their schedule and comfort.
We left our gofast in Florida for an entire summer, and either hurricances, very poor weather or work got in the way of making it across the stream. If fortunate to be living in Florida, then it is a whole lot easier in picking the right conditions to cross. If you have a weekend off, and fly down to the boat, you are going to make the go/no go decision in less than perfect conditions much of the time.
I am also thinking ahead to when Cuba opens up. Now you are going from 40 miles across the stream to 90 miles from Key West. The weather you start with can change into something nasty halfway across. I know if I have stabs on my boat they are going to fail at the worst possible time, hence I don't want them. <gg>
Pascal took a picture of us leaving No Name Harbor (Miami) after 60 MPH winds the night before, as we are headed into 20 knot+? winds and a dinner date in Fort Lauderdale. Many people have told us we should have been sailors since we go out in all kinds of nasty weather. The destination is the key. Yep, it was cold, and this picture is unlikely to be used by the Miami Tourist Bureau <gg>.
The gofast may look odd, because I totally customized it for our purposes. It has flip up side rails, fishing chair, rod mountings and rear box for fishing 20 miles off the Fire Island, NY coast. Everything folds or is removeable within munutes, to return to gofast "cushion on engine hatch" configuration. Hence the name. The boat also turned out to be great for long distance cruising, NYC to Nantucket etc. Fantastic to run around in. When our plans were different, I was pretty sure I was going to tow it behind a 58 Hatteras cockpit motor yacht. Now, it really looks like a Hat. SF makes more sense for our future activities. I am in no great rush to change boats though, and it took about five years to decide this boat was right for us to purchase. Same deal for the next boat.