looking for basic advice for someone thinking about a boat.

How much do you want to spend on the boat?

How much can you afford for annual maintenance?

How many people will be on board with you?

Not knowing much more I'd say maybe you should consider 40-50' sail boats a few years old. If conditions are right your operating costs can be near zero.

Here's why that price: 1) it's wood, 2) it's 40 year old wood, 3) never heard of the maker. It looks like it started life as a commercial boat of some kind, 4) it's wood. The next owner may well be using it to heat his home (in his fireplace). There is no free ride, especially in boating.

Hi,

Before you get your hopes up to far about being able to subsidize your life style with some casual charters you might want to look at the restrictions on non Thais conducting business out there.

Greetings,
I've heard it said-Buy the smallest boat you can afford. Meaning, your $100k can buy you either a say, 1960 100' wooden vessel (LOTS of upkeep) or a 1990 40' vessel (better shape, less upkeep/fuel/maint').
Peter.

With no experience going into boating, you can pretty much forget chartering under any circumstances (regardless of Thai laws, size of boat, how well appointed it is).

There are lots of old salts (and young salts) operating their own quirky, funky charter boats but they've been boating their whole lives and can fix anything anytime anywhere.

To think you can subsidize a very thin retirement budget by picking up charters is pure fantasy. Are you an expert diver? An expert fisherman? An expert naturalist w/ local knowledge of flora/fauna?

Any one of these might be a basis for your own particular kind of charter business, but having none of them and no boat background (no knowledge of operating expenses, fuel costs, boat materials, size of boat, sail v. power) is a recipe for burning through your cash in a hurry and finding yourself back in the market looking for work when you'll least want to...

I think that a misquote of a real estate axiom, i.e. 'buy the worst house in the best neighborhood you can afford'. With boats I always recommend that if people are considering 2 boats, buy the bigger and better one. If you're thinking of it today you'll probably be in it within 3 years with an extra broker's commission. Of course you must have a realistic budget for maintenance, operating and living expenses. Then double it.

Hi,

Pretty brutal and basic which is exactly what the guy was asking for.

OP stated that he is looking to retire in 10 years from now. That should give him plenty of time specializing in a certain field.
This is the boat I would be looking for.

I have a friend who has cruised the world on a 40 ft sailboat for the past 15+ years ... he makes virtually all repairs himself and enjoys a sensational life compared to many. He currently keeps the boat in Langkawi Thailand ... when he visits the USA annually, his Thai girlfriend lives on and looks after the boat. He spends time in Laos, Cambodia and often runs motorcycle tours for tourists. He speaks the native language like he was born there!

He laughs at the kind of dough I spend on my powerboat. I would definitely be looking at a sailboat if I were you ... he likes catamarans too but does not have one.

One fight with the girlfriend can make a 40' sailboat very small indeed. Which may explain the GF as opposed to wife. Next time he laughs, inform him that you can have breakfast and dinner at home and (an expensive) lunch 50 miles away. Try that with a snailboat.

Langkawi is Malaysia, not Thailand.

I like OP's idea.
Retire from the rat race and retreat to a yacht in a nice tropical location.

I've met quite a few people who do so but most of them live on a shoestring budget. I would try to find a job you can do on the side. As OP stated Dive Instructor can be one of them. Doesn't pay much but enough to live on when the boat has been paid for. It also allows you to stay in touch with society. From freelancing for a diveshop you could build out into chartering your boat etc.
With WiFi internet almost being everywhere nowadays (and for sure in 10 years from now) you have a lot more possibilities to supplement your income.
You've got to have something to do. Many of the retired single boaties I've met hang around the marina bar whole day long.

Living expenses can vary. Anchoring and eating local products vs. marina berthing and eating imported western brand food makes a huge difference.

If choosing for a sailing boat you've got to consider the fact that you're near the equator so you need something that get's you moving at 10 knots of wind.
I would avoid boats with minimal exterior space, being inside requires aircon and aircon is expensive. Better the open deck of a cat covered by an awning.

You still have got 10 years from now to think and dream about. Just don't make the mistake of getting involved with woman who are not into boating in the meantime because that could destroy your retirement plan once and for all.

Just about everyone that takes a resort course has this dream. Lots of competition. To give some comparrison. I used to know a fishing mate (similar dream) who worked a good charter boat in Ft. Lauderdale. He told me he knew 100 ways to cook hot dogs. He used to go to the Sabret outlet, get 10 lb. bags and they were breakfast, lunch and dinner for more than a month several times.