I ideally plan to start in Virginia and go round to Alaska, ending with a tribe I work with there. It isn't fully around the Americas. I am looking at a 45ft seawolf, Bruce Roberts 44 offshore, Reliance 44 ketch, and Columbia 43 all for under $20k. Maybe none of them are ideal with more research.
As others have noted you are proposing to sail a long distance, and some of that sailing will be in very tough sailing venues. Those kinds of distances in those types of conditions truly age a boat. The resultant wear and tear of that kind of voyaging can easy be the equivalent of 10 to 20 years of normal boat use, and 10-20 years of normal boat use is enough to wear out several sets of sails, pretty much all standing and running rigging, much of the deck hardware, and minimally require some engine and transmission work. The bigger the boat, the exponentially larger the cost of these components. And those are very large boats that you are looking at.
Disregarding for a moment the suitability of the individual boats that have expressed interest in, if you were lucky enough to find a 45ft Seawolf, Bruce Roberts Offshore 44, Reliance 44 ketch, and Columbia 43 for under $20k, which also had a sound hull and deck, and reasonably intact interior, and rig, to make the kinds of passages that you are proposing, that boat is still likely to need some mix of new sails, all standing and running rigging, much of the deck hardware, and some major engine and transmission work, as well as updated electronics, galley gear, some new hoses and wiring, a proper inventory of spare parts, and so on. Collectively, some partial list of those items would cost minimally somewhere in the $30,000 to $60,000 range and that assumes that you are good with your hands, and have the time to do this work without paying professionals.
It is important to understand that a good designed, structurally sound, and moderately well equipped older 44 footer will typically sell in $40,000 or more range and typically well more than that. An older version of a design that is suitable for distance voyaging and which is anywhere approaching a ready to go condition will be closer to $100,000 and even at $100,000 those boats are likely to need some additional improvements that the improvements alone could easily exceed your $25,000 budget.
When I look at the list of boats that you are considering, they are as scattered in their design intent as bird shot fired into a gale. Normally you would not expect to find these boats on the same candidate list unless the criteria for that list was solely "Boats 44 feet and over that can be bought for less than $20,000." As a quick run down:
45 ft Seawolf: Old school (as in slow and physically demanding to sail). Build quality varied widely on these boats from worse than junkie to halfway decent. These are boats that do not sail well in light air (meaning that you end up motoring a lot of time) and do not do great in heavy air, tending to be rolly and tender relative to drag. If you found one under $25000 it probably needs new decks, masts and deck houses, which were wood on most of these boats.
Bruce Roberts Offshore 44: Design wise this is probably the best design on your list, and depending on the hull material, this was one of Bruce Roberts best designs from that era. BUT (and this is a big BUT) Most of these were either owner built or owner completed kits. There were fiberglass kit versions of this boat that had decent glass work. Most of those were owner finished and so the build quality varies wildly. Compromises were often made on such basic safety items as ballasting (iron boiler punchings in concrete rather than the intended lead shot in slurry), internal structure and framing, rigging engine size and placement, electrical and plumbing systems, propane systems and so on. The owner built boats, and especially the steel, ferrocement, and plywood versions should not even be considered.
Reliance 44 ketch: I know that this boat has a strong following in the traditional boat world, but design wise, the Reliance and the Seawolf would be at or near the bottom of any list (as in below the cut off line of "maybe passable in a pinch") that I would consider for the type of voyaging that your are considering.
Columbia 43: These were some of the best boats that Columbia built and probably the best sailing boat on this list. But they began life as racer cruisers and are a little light for the purpose. If you found one for less than $25000 it is likely to be a project boat that is shot or close to it. A Columbia 44 in that price range is likely to need keel bolts, deck core repairs. remedial structural work, chainplates and so on. One knock on this boat is the Vee-drive which makes it really hard to get to the stuffing box.
But more to the point, this is not an undertaking that should be considered lightly. These are big brawny boats that take a lot of skill to maintain and sail. Clearly, by your own admission you do not have the sailing experience to pick out the right boat, equip it and handle it.
In an ideal world you can find an experienced sailor who would be willing to help you find the right boat, put her into shape, maintain it and act as skipper for food,board, and the adventure of it all. People like that are getting harder to come by but they are out there. Overtime you would ideally learn to become a decent crew, and maybe a decent skipper.
There was a period when several times a month I would receive an email from someone who is considering doing something similar to what you are proposing. I have watched literally dozens of folks go through this. Some are successful in getting 'out there', some discover that they really enjoy sailing and find that they really have no need to 'go out there’; some have discovered that the sailing life is just not for them, and others have not even gotten past the dreaming stage. I apologize that this is a little long and was written when someone else who was just starting to explore moving onto a boat and use it as a base of operations. I respectfully suggest that it might provide a foundation upon which to build an plan that hopefully works for you.
"From what I have seen, the most successful would be cruisers have been the ones who have been somewhat systematic about going. There is a lot to learn before one can safely venture offshore. No one would assume that they could buy a jet airliner take a few lessons and be able to fly around the world. I think most rational people would expect to start with a small plane and work their way up. But for some reason people assume that they can just go out and buy a big boat, take a couple lessons, read a few books, and then go safely cruising.
While there are people who literally taken a few lessons, read a few books and gone out cruising, those that were successful following that route are far more rare than those who have done some kind of apprenticeship. Learning to sail and learning to cruise involves a lot of knowledge and no matter how much you know, there will always be more to learn, but I suggest that you at least take the time to learn the basics, and that just about can’t happen if you buy ‘a big sailboat’ and try to learn.
I find myself saying this a lot lately, but here I go again. We all come to sailing with our own specific needs, our own specific goals and our own specific capabilities. The neat thing about sailing is that we all don’t have to agree that there is only one right way to go sailing. There is no more truth in expecting that there is one universally right answer about many aspects of sailing than there is in trying to prove that vanilla ice cream is universally better than strawberry ice cream. One area of sailing for which there is no one universally right answer involves the amount of knowledge one requires to go sailing. The other is what is the right boat to own.
For some, all they need or want to know about sailing is just enough knowledge to safely leave the slip sail where they want and get back safely. There is nothing inherently wrong with that approach. Lack of knowledge will impact the level of risk, cost, comfort, and performance, but if you want to get out there with minimal knowledge it can be done. But for others, like myself, there is much more to sailing than simply developing a rudimentary knowledge of sailing basics. If you fall into that camp, it is next to impossible to learn to sail really well on a boat as large as the one in question.
While I am in no way suggesting that this makes sense for everyone, for those who really want to learn to sail well, I strongly suggest that they start out owning a used 23 to 30 foot, responsive, light-weight, tiller steered, fin keel/spade rudder (ideally fractionally rigged) production fiberglass sloop (or if they are athletically inclined then a dinghy.) Boats like these provide the kind of feedback that is so necessary to teach a newcomer how to really sail well. Boats like these have small enough loads on lines and the helm that you and your children can all participate and learn together. If there are other people involved, especially if there are children, being able to learn and participate, everyone will be more engaged and less likely to be bored and feel kidnapped.
By sailing well, I mean understanding the nuances of boat handling and sail trim in a way that is extremely difficult to learn on a larger boat. Used small boats generally hold their values quite well so that after a year or even few years or so of learning, you should be able to get most of your money out of the small boat and move on to a bigger boat actually knowing something about which specific desirable characteristics of a boat appeal to you as an experienced sailor rather than the preferences of some stranger on some Internet discussion group.
From the advice that you may have already received and are likely to receive you can tell that there will not be a consensus of opinion on how to go distance cruising.
In any event, I would suggest that at the very least you try to get some sailing lessons. If I were in your shoes, I would sit down and put together a list of all of the things that I would want to know before setting off voyaging such as:
• Boat handling
• Sail trim
• Rules of the road
• Boat husbandry, repair and maintenance
• Diesel/ gas engine maintenance and repair
• First aid
• Heavy weather tactics
• Legal restrictions on leaving and entering foreign countries
• Navigation, (Piloting, Celestial, dead reckoning and electronic)
• Radio operators license exam requirements
• Safe and dangerous fish to eat
• Survival skills
Once I had what I thought was a complete list, I would set up a schedule to try to develop those areas of skill that I was currently lacking. As much as possible I would try to involve all those involved in as many of those aspects as each is capable of understanding. This process could take as little as a year, but more often takes two to three years. The process itself can be very rewarding and can build the kind of bonds that are required to be cast away on that oh so small island that a boat underway represents.
After sailing for a few years you should be able to further define your goals and develop your own sense of what is the right size and type of boat to do what ever you decide to do.