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That said, the main idea I am trying to get straight in my mind is the following. I am interested in buying a decent sail boat, something to the maximum cost of $100,000. It has to be a boat that I can also live on when moored in the marina. I intend to use this as a permanent living space for a few years, since at the moment, the place I live and work has very expensive housing, I pay something around $16,000 per year between house rent and utilities, so I was wondering if I could use my savings to buy the boat, and spend a portion of what I spend now for rent and such, to live on and to maintain the boat, and pay for fuel, repairs and mooring. The city I intend to move to will have much more expensive house rents and utility costs, so on the long run I believe the investment will pay off, at least for the next few years while I am still single and can afford to spend my time on the boat.

So what do you guys say? Is the life on a boat fun? Or something that should be avoided? Does my idea make sense? What boat would you recommend for a newbie to the sailing world, to live on comfortably, and to learn the ropes of sailing, and hopefully someday to sail on bigger waters and go on week long cruises?
Buying a boat to beat land based housing costs is likely not going to work. You did not say what city you plan to move to, but Even with no boat payment, slip and electric, sometimes water and a liveaboard fees can easily get to $1K a month or more, especially in a sailing center like Annapolis, Marina del Rey, South FL, etc. If you are looking at NYC and can stay on the cheap at Lincoln Harbor in Weehawken, NJ....slip alone is going to cost you a boat payment and will rock and roll you all night. Been there, done that. But compared to a condo in Hoboken or Jersey City, you may come out ahead.

IF you can stand being an hour away from walmart, places like the northern neck of VA or Oriental, NC will be half or more of that $1K.

Living on a boat is very unlike living in a house. It CAN be fun, but it is often challenging, stressful and you are almost living in a glass house, so you always have people "peeking" in - sometimes even aboard. Then you have slipmates, as living on a mooring presents it's own set of challenges, who may or may not be good neighbors.

We, the wife and I, found it to be one of the greatest things we have ever done, and this was in a marina that set the rules as they went along, a decent marina makes a difference. You have to be flexible and very willing to experience new things. Like getting up in the middle of the night to check lines, that don't sound right...or not screaming or falling off the pier, at 2am while walking to the bathroom and being startled by a heron or kingfisher who was as startled as you were. Getting water in the winter was a challenge for us, as marina manager ignored the schedule he set, leaving several piers with out water....no, it had not frozen, he just liked being in control.

For a single guy, you can buy a LOT of boat right now for a hundred $K. Were it me, I would look for the best $45-50K boat I could find, and be sure to look at dozens of boats with at least three brokers, and set the rest aside or in the bank. The mass produced boats are fine for what you want and a 35-36' would be just dandy...that size usually gets you a decent berth, a decent head and enough kitchen to "bachelor" it for long term.

An old (mid 80's) premium builder's boat, like Sabre would be decent as well. Just look and be sure to get your own survey.

Best of luck.
 

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..... happy to pay less and invest the rest into something else :p
I forgot, but this one is a biggie....never mistake a boat (or let a broker or dealer convince you), of any kind, with an "investment"...unless it is an Oyster, Hinckley, Swan, etc - it is a depreciating asset, and always will be.
 
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