Originally Posted by 7tiger7
So I'm thinking I could sell the boat here in Boston, where there is a slightly stronger boat market, and then move Tampa and either buy a house or a large trawler and live aboard for a while...
A house should increase in value over time assuming we don't fall into another housing value hole. Prices are low in this area (Puget Sound) but the demand for housing has outstripped the supply so house prices are starting to reflect this. At least so say friends in the real estate business.
A boat will decrease in value over time unless it's a vintage collector boat like a Gar Wood, Hacker Craft, Chris Craft and the like. So I don't think a boat should ever be viewed as an investment. It's just a toy. Even if you live on it, it's not an investment in the sense a house or property are.
Living aboard a boat in a place that often has good deals on hurricanes does not seem a particuarly smart thing to do although I'm sure there are plenty of people who do it and enjoy it nevertheless.
How much time to you use your boat now, and how much time do you anticipate using a boat in Florida? Do you work and if so does that work tend to limit your vacation time?
How much do you like your current boat? Since selling it is something you're willing to entertain I'm guessing you're not super attached to it. The people on this forum I get the impression are attached to their boats don't seem to think it's any big deal to run them up or down to where they're going to be.
So if you're not all that attached to your boat perhaps it makes the most sense to sell it, buy a house with good resale potential in Florida and charter a boat whenever you have the time or the urge to take a cruise. If you anticipate spending more time helping your parents as time goes on, something like a boat tends to take a back seat. And while it's in the back seat, it can have a tendency to deteriorate some and cost you a bunch of money when you have the time to get back to it.
So lots and lots of variables and you're asking people who don't know a thing about you or your financial, work, retirement, etc. situation. So the bottom line is that I think you should do whatever your gut tells you is the right thing to do.. That's always worked for me when I've had major decisions to make. None of us can or should make that decision for you, or even should really be trying to "help" you with it even though it's always fun to tell someone else what we think they should be doing even though we don't have a clue what we're talking about.
PS---I'm not looking for you to give me answers to the questions I posed earlier in this post. The answers are none of my business and I'm not particularly interested anyway. I posed them because I think they are what you should be asking yourself if you haven't already. Because your answers to those and a host of other questions will --- along with what you feel in your gut---- define for you what your action should be.