looking for basic advice for someone thinking about a boat.

That's Fort Lauderdale, a saturated market. Not to be compared with all the nice places opening up for boaters in SE Asia.
There's always something to do and ways to earn a living but in saturated markets you'll have to stand out of the crowd due to the competition.

The hardest part of living this lifestyle is to remove the chain and shackles that keep you doing what you do. Partner, children, mortgage and 'friends' who envy your choices but are to afraid to live their own dreams.

I have done a similar thing in the past, relationship finished and the opportunity came to sell the business. I booked a single ticket to as far as I could get and with all personal belongings in storage and a nice credit on my bank accounts I left. It's like jumping in the deep end of the pool but the feeling is so liberating I can only recommend it.
The only restrictions you have are in your head.

Not sure how it is today, but back then the only thing they were saturated by was German tourists with full pockets. 10 boats in a town with 100 tourists or 1 boat in a town with 10 tourists, it's all the same. Not that there aren't good times, and some very successful businesses, but reality is way different than the dream when the rent is due.

oops

Yes ... the friend who has been doing this for 15+ years will not allow the "shackles" ... hence, girlfriend remains just that .. and no kids.

Not that I envy the lifestyle because I enjoy my family tremendously and choose to work with the boundaries that go along with family.

Mike

Hi Greylon

May I respectfully recommend you DO NOT purchase a woody... unless you are EXTREMELY well versed in a wood boat’s needs/requirements/mandates (especially older wood boats), e.g. nearly-constant general up keep, often-deep maintenance procedures, and at-times full-on sectional repairs, i.e. complete transom replacement, total bottom refastening, portioned keel splice, bow stem replacement, salon frame repair, gunnels repair/replace, deck repair/replace... etc... etc...

Back in 1960’s - 70’s I spent much time on craft cruising the North Atlantic waters and working in New England boat yards with shipwrights – we nearly always worked on wood boats... because fiberglass was pretty new and seldom needed any repairs “back in the day” – LOL! There were all forms, sizes and types of great wood craft (BTW, Ditmar-Donaldson is a well built wood boat).

Believe in others’ and my counsel, if I may repeat, unless you are EXTREMELY well versed in a wood boat’s needs/requirements/mandates... I recommend you DO NOT purchase a woody! At end of my young boat working life I also spent a year in a new boat fiberglass manufacturer.

Currently I own a great condition and completely original 1977 34’ Tollycraft tri cabin; she has superb fiberglass construction and layout. My family simply loves it. We spend long weekends cruising and/or hanging on the hook around SF Bay and inside SF Delta areas. We don’t at all live on our Tolly, but, my wife and I do plan to purchase a mid 1970’s to early 1980’s 48’ Tolly in next few years for cruising to Alaska in spring/summer and Mexico in fall/winter; in between SF stopovers.

There are many affordable craft considerably larger than ours and in our band of other exceptionally well built fiberglass brands

For ease of living and best value retention, I recommend finding a VERY well built fiberglass boat, power or sail. By well built fiberglass I mean:

1. Hand laid, thick and solid (no cored balsa, foam or plywood cold laminates) fiberglass hull that used the best fireproof resin and has deeply impregnated gel coat
2. All decks and all superstructure fiberglass (cored is ok if done correctly and with best materials)
3. Railings stainless steel – no wood to care for if possible

In today’s market there are some good prices on fairly large and very well built older fiberglass yachts. Research and knowing how to cut a deal always helps.

There are soooo many other items to mention or discuss! If you want to chat send me a personal message and I’ll give you my phone # for a chat.

That said... I love your gumption... the fact you are planning a decade in advance for early retirement on a yacht is super.

Get It On – Keep and Complete Your Water Liven Dream!! When we keep moving forward there is little time to bother to look back!

Happy Dreaming... errrr... Boating - Art

Having to share your adventure, your partner/wife must (repeat...must) be fully supportive of the idea and the chosen vessel. As insigator of adventure and vessel quest (plan A) you must be prepared to bail out and definitely have that as plan B that has been thought out in advance. It may have been said before on this thread but it bears repeating: "If moma ain't happy, ain't nobody happy! And it gets worse if the skipper ain't happy.
Cheers, Richard.

New Lifestyle & Wooden Boat

Been there, done that a couple of times in my life. It is liberating. But remember it gets a little tougher to do as you get older.

You don't necessarily have to be as concerned with wooden boat ownership/upkeep in Thailand as in the USA, particularly if you don't intend to keep it in 'Imron yacht condition'. There are lots of Thai fishing vessels that are built of wood, so there are lots of local boat yards that can do maintanence work on wood vessels. Naturally it would be best to start out with a good one.

That wood fishing vessel you sited above looks to be a lovely liveaboard, but it night incur a fairly high maintanence expense

Why?
You know what you pay for a domestic helper who takes care of you 24/7 and healthcare in Bangkok is probaply better than in most western places.

'Imron yacht condition'. There's a new one on me. What ever happened to the term "bristol"?

Bristol to me always evoked 'varnished finish' which you certainly don't want to try and maintain over there in that sun. So I thought the next best description might me those yachts that try and maintain that beautiful topsides paint job with no flaws, which in a wooden vessel might present its share of problems as well. And either of these might require hi profile yacht yards.

South East Asia in a Converted Fishing Boat

Now here is more down to earth discussion:

Trawler Conversion - Cruising Under Power - South East Asia in a Converted Fishing Boat
http://cruisingunderpower.fastmail.net/

Ditmar-Donaldson was a legendary wood boat builder in Costa Mesa, CA. I'm not sure about your plan in general but as far as that particular boat... it's probably still going to be around after everyone reading this post is long gone.