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mrsrobinson said:
I would trailer the boat down. Nothing has changed in your lifestyle/family size/boat needs, correct?
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Florida may open up a whole different type of year around boating than what you have experienced in the north.

Sounds like your current boat is a "known quantity". Wouldn't want to sell it immediately, but I would want to make sure it was the type of boat that I would want in Florida before incurring the expense (and time) for the move.
 
When I first read this post I wasn't sure how to take it, actually checked to see if you were a real person or not (Sorry). Your post is all over the place, which to your point - is where your at, at the moment. Been there recently myself.

I recently did exactly what you are talking about and did it all in a few short months. We were looking at places around the Chesapeake Bay for years prior to our actual move for possible retirement. A new position opened up and made that move a reality. So it's January and started the new position in march. Spent the next two months finding a house and setting up the move. Sold two house in NY and closed on a house in April in that time frame. Now had to get the boat down here at the same time as moving and packing etc. man that sucked. Ended up taking a week off to deal with it all and I only moved five hrs south of where I use to live.

I will say this, as far as the boat goes, pay to have it transported. You will go through the same amount of money or more to drive it yourself and you will need to follow the weather while your traveling, a 27' boat in the ocean for long periods of time may not be the best thing to do while your trying to get settled in to your new surroundings. Plus it will take you the better part of 8 days coming down the Hudson etc. and down to FL. Maybe 6 if you push it, but you get my point. Not to mention have you ever done anything like that before?, if not do not even think about it. Yes, depending on when you go you might get 7-8 days along the eastern seaboard of perfect weather ...

I guess you know exactly where your going, so get on Zillow and find an apartment, unless you have dog's. Then you will need to find living quarters that you own. I myself have never been ok with renting, always thought of it as throwing money out of the window. So if you have that mind set, like me, you have a house/condo in your future. Not sure your time frame, but I would think it's happening as we discuss this. I could not imagine making things go any smoother then it did for me, I literally had every single step go right and all of the timing of selling and buying was to the day, couldn't do that again if I tried and it took me three months to put selling two house and buying another one in motion, one month to plan and make the move happen (including the boat) for the following week after the closing. The boat was the only thing that didn't go smoothly and cost a small fortune to move it here.

Good luck with all of the decisions you have in front of you.
 
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My two cents - you need to find a place to live on the hard before you figure out what to do with the boat. Get an apartment if you don't want to buy. Raising a family in an apartment would be 99.87% less frustrating than on a boat. Further, if you think $350k for a house is ridiculous wait until you start shopping for that Sedan Bridge that runs well enough to get in/out of the water when the hurricane comes. You said you don't want to live in garbage. I'd imagine that's exactly the kind of boat you're going to end up in if you're trying to save money.

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Jus Cruisin said:
I've mentioned in other threads. I lived there (Bradenton and DeBary) nearly 30 years and I saw a lot of northerners not be able to handle the summer (pretty much 6 months) weather and bail. If they didn't move back to where they were from, they'd become "halfbacks" and move to the Carolinas north Georgia, Tennessee areas....
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I lived in Puerto Rico and Phoenix arizona. I am not bothered by it. I totally appreciate what you're saying though.
 
If you are moving for work, I believe the moving expenses are tax deductible. Depending on tax bracket, this could reduce the shipping cost of the boat 30%.

Tim
 
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