This is the boat I'm looking at buying

This new ship sure is pretty. Without the time (near full time) you will be behind in required maintenance and loose any value you THOUGHT you had.
On the other hand, there are good looking plastic Commanders on the lakes, less money asking, less maintenance, cheaper to ensure, and probably less consuming of time and money to ship by truck.

OR, buy a boat on the left coast.

No do not see pics on the trailer and coming off. Witness it first hand along with the disassembly and reassembly. You mark every connection to insure line up. There have been more than a few nightmares.

olderboater has taken the time to give you the bitter medicine here, but I would say "we" should view your posts for this: you have a dream to own something that you could not afford if or when it was new.
Now it is at a price that is so affordable in comparison that you are smitten. Trouble is Doug, this is a boat, not just that but a timber one.
This is a common problem for many of us. I have seen so many beautiful vessels over the years in wood, fibreglass and FWIW, right now I am researching a cold moulded hull. Plus, I have been offered a beautiful classic 72' which is in wood and even considering that. There is usually a next boat scenario in my family.
So you are not alone on this issue. But you must get realistic with the advice given here, or we are wasting our time.
The simple issues that you are not addressing are that, purchase price aside, the maintenance and other costs that made this a very expensive hobby for the original owners are still there now. Except these costs will be even more now that the boat is so old.
Sure you can cover many issues with your own labour, but certainly many will remain.
Can you afford these, week after week and still use and ENJOY your boat!
How long before the novelty of spending the weekend working in the bilge wears off
Can you afford the time away from family and others etc?

I own a 1970 model boat. It was totally rebuilt with new or re-conditioned equipment by Merritts in Florida, so it is more like a 2001 vessel and let me admit, I spend a huge amount of time keeping up with maintenance and love it. But sometimes not.
It has cost me FAR more than most the other boats I have owned.
Keep in mind, it is fibreglass, as in 1970, when Fibreglass was laid real thick.
I have owned over 20 boats from 23' to 65'. Some brand new, some a few years old, but none more than 3 y.o. Purchase prices from a few thousand to over $1 million. I understand the emotive side of the purchase and have experienced the holding costs.
Unless you have the disposable time and disposable income, you will probably find that within a few years your dream is being listed on a sales website for a "giveaway" price just as it is now, where it will sit for a long time deteriorating until the next dreamer comes along.
Meantime, enjoy the experience.
Cheers.

If you're thinking of taking it by water, even if to Fort Lauderdale, and then shipping it, add much more money to my deduction. You're talking a minimum of $60,000-$70,000 and I'm thinking by the time you repair everything along the way you could add another $20,000. You're talking about a trip beyond any this boat has ever taken, even when it was new and in good condition. If you're thinking of taking it all the way on it's bottom, my question would be "how many months can you afford to be stranded in Nicaragua (I could have picked any country along the way)?

If you think you can maintain this boat for $5-10,000, think again.

How in the world do you think you're going to insure this boat for that trip?

$5k to $10k per year to maintain? Not a chance. Based on the content of your posts I believe you are someone who is just dreaming on the inter webs.

But people do crazy things with money every day so if a classic wood boat is really in your dreams look at least around the PNW for one. You can't swing a dead cat without hitting an old woodie up there, plenty of boats to choose from and you will save yourself the most fantasy filled part of your fantasy which is transporting an old wood boat thousands of miles by land sea or air I suppose. Any way you slice it transporting will probably cost more than the boat and or destroy it.

Your idea about loading it on a ship at Port Everglades and off loading in Ensenada made me spit up my drink. And I wasn't even drinking anything.

No way she goes overland intact. Seems we just had a discusion with someone here with a very similar boat, maybe a 46, within the past couple weeks. He knew the top needed to come off and was searching for someone capable of doing it.

I'm really not sure how to read you. At first I didn't think you were serious, because the endevor doesn't make much sense except for a collector. But your not blinking at the cost of transporting tells me you are. That said I think your projected maintainance budget is way low. Also, by the time that boat gets to L.A. you'll have probably laid out $200K or more for a boat that may have almost no resale value.

But that's after survey and correction of any survey issues. Also, they will sometimes put limitations on the boat depending on the survey.

BTW, you might look into loading the boat in Montreal. Dk about the logistics or cost, but would be less wear on the boat if there is a route that works.

It would be a crime to move this boat to salt water. She should be in a museum.............

Agree.
BTW, we've losely discussed the maintenance costs of a boat such as this, painting and such, but we neglected to consider one huge item. I just looked back through the pics. There's a huge amount of really fine varnish work. How are you with a fine oxhair brush? This boat has spent its life in fresh water, way up north and under cover. Southern sun? Salt Water? Painting is not my thing, but I think you're looking at easily a month's work and maybe $10,000 a year just for that. Maybe one of the finish guys will chime in with a more professional estimate.

I don't think you'll even get a response at $50K. This boat is an 'if you love it you pay what I ask'. I'd guess he's seen a lot of $50K offers since 2010. Besides, the asking price is the cheap part of what you're proposing. So if you love it, just buy it and keep your black card handy. Nothing about this deal makes sense. When that happens people end up married, owning works of art or owning classic boats. Sometimes it even works out. Other times it's fine as long as they can afford it. If you were buying this with a thought to living cheap you'd be in trouble. As long as your pockets are deep and you're doing it for love, go for it. At this point you know what you're in for.

Would you do better purchasing a Connie already or part way there? Then fixing her?
It's not like a shortage of Connies already on the Left coast market or half way there.

Last one is a nice plastic boat in Texas.

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You're missing the boat completely. The purchase price is irrelevant. There are no comps. It's whatever you want to pay.

The point is it doesn't matter. The purchase price is only the cover charge to get into the club. It's your bar tab that's going to get you.

If you spend $75K on it, you'll have $160K to 175K in it by the time you get it home, if you get it home, unless you consider transporting it over land which requires removal of the upper structure.

If your plan is shipping from West Palm to Ensanada, then you're talking $60,000. You're still talking about running it 1700 nm. With stops and delays that will cost you at least $12,000 crew plus $2,000 expenses. It will cost you $10,000 for basic fuel, fluids, filters if everything were to go perfectly. That's $85,000. Now, it will cost you a minimum of $10,000 to get it ready for the trip, just doing the minimum. On top of that, I'd plan on spending at least $10,000 for repairs and maintenance on the trip. So now you've added $105,000 to what you pay to get it home. Oh and toss in the cost of survey and insurance to that including tow insurance.

You're still assuming the boat is ready to jump in and go. I'm assuming you'd keep it on the hard in Michigan for the winter or do you think you'll buy it, survey it, insure it, find a captain and get it through the Erie Canal in less than 2 months? You'll need to get the A/C and Heat serviced as it will be a cold trip. That system is 16 years old. Are you calculating the cost of replacing a 20 year old plotter and perhaps even radar? You'll have to get zincs changed before starting the trip. The hot water heater is 18 years old. That's dubious. Then servicing the 18 year old generator and the 19 year old engines. Replacing all impellers and filters. This then assumes that no hull work needs to be done, which I'd expect some to be needed.

I suggest you make an offer since you're set on it and get the survey done. Then if you pay attention to the survey and all that needs to be done plus cost the transport you'll be lowering that offer post survey.

See, there is no fair price to both you and the seller when you're talking about transporting to California by water. $60k to 75k would be fine if you lived in Michigan and intended to use it there. But it can't end up fair. Someone has to pay for getting it from there to LA. That's the problem $70k to transport means it's $70k from being fair. Either you overpay $70k or he sells short by $70k or some split. That's the gorilla in the room that you can't get past. $100-110 may be fair to the seller and $30-40 may be fair to you. Anywhere more you're overpaying and less he's selling short. You pay $75k and you'll have more in it than his asking price by the time you get it home. And that's before you start upgrading, paint the bottom, refinish the wood, and do all the other work.