AllanR77,
If you are still around, I hope you'll update us on how things are going.
Few thoughts ...
You sound like a practical sort of person who is able to figure things out for yourself, so I will come at it from a different perspective. First, let me tell you, I'm not that experienced either, so keep that in mind - my situation is actually quite similar to yours in that I am still trying to learn all of this as I go along.
Having said that ..
I think it is good to divide things up so you can focus in on what's important. Sailboat design
is very complicated and requires a lot of experience to understand, it is hard for us beginners to know which boats will do well on the ocean as a result. The operation of a sailboat
can be complicated depending on the situation, there are a lot of tricks and techniques and few people have mastered a significant number of them, again, experience is what its all about, learning to sail the boat. Sailboat maintenance, however,
is not that complicated, but is further complicated by the systems you have on board.
Maintenance
The maintenance you'll probably have no issues with. The basic boat with a full keel is simple - hull, mast and rigging, rudder, and sails. Being in the military you should have no problem learning new skills in a methodical kind of way, and the skills you need for the hull are such things as repairing fiberglass, sanding and repainting the bottom, waterproofing things that need waterproofing and that kind of thing. The rigging you can also learn from someone who knows about it, volunteer some time with a rigger and learn the ropes maybe ? In essence it is just wire holding the mast up, and once you learn the basics of rig tension, swaging, etc, then you've got it, it absolutely is something you can learn and for the most part do yourself. The rudder does sometimes have to be serviced, but again, it is just a thing that only has so many parts, and you can learn how it works by taking one apart and putting it back together, etc, maybe overhauling it when you get your boat is a good way to go. Finally, the sails, you can get into the sails as much as you want to - one of the first things I bought was a sailor's palm, needles, etc, you can learn a lot about this from books, but its mostly learned by doing it. Once you have these basic skills then you can pretty much take care of the boat yourself with the occasional need to use tools and techniques that you may not have, like a crane, or careening the boat, etc. You can, of course, spend all kinds of money having other people do these things, but that doesn't sound like what you are thinking, which is good if you are trying to control costs.
You can, of course, quickly get very complicated with sailboat maintenance. Add in an engine and you need to know about engines, become a diesel mechanic, etc, but again you can learn these things with study on your own or by taking classes. You'll no doubt want to use electricity, so its time to learn about solar panels, wind generators, electrical wiring, and all of that, again, it can be learned. Radios for communication, now you might want to investigate getting your amateur radio license, learning some basic electronics, learning about antennas, maybe start hanging out with amateur radio people and practicing with the gear, that type of thing. Every system you add (add to the dream boat in your mind, I mean, you may purchase it already installed), every system you add increases the complexity. Of course a lot of these systems are not necessary for operating the boat, so if they break it may not affect you that much and you can fix them at your leisure, but if you grow to depend on them then you'll have to maintain them and keep them working.
Operation
Sailing the boat is another set of skills that can be complex, but isn't that hard to learn the basics. I think I read somewhere that someone said that the skills required to sail a boat can be learned in minutes but it takes a lifetime to perfect them. Here a little training might help if you know absolutely nothing about it, but experience is probably the best teacher, and simply having a boat of some kind to practice with is probably the way to go. I am sure you will be able to figure it out, even if all you have is a book to learn the theory from, it just takes a little time and practice. Again, it is a series of skills that for the most part can be learned, using different sail combinations, being able to fly a spinnaker, etc, but I'm convinced that it can't all be learned, the ability to navigate, for example, just seems to be something you either born with or not.
Some suggest sailing smaller craft to learn the basics of sailing, a dinghy for example, because they are quicker to react and you can really get a feel for sailing with small craft in a way that you can't on a bigger boat, I think there is something to this. Another suggestion I have heard is to enter the racing scene at least as crew because the racers will teach you all about what good sail trim is and that kind of thing, valuable information to have. Yet another suggestion I have heard (or read) is that its good to practice sailing without using a motor at all because that forces you to do the kinds of things that you will have to do if your motor fails, here again there are many specific skills you can learn such as sailing on and off anchor, docking without motor, etc.
Anchoring and ground tackle is another area of operation you will have to learn, and there are some good books out there on that subject. Some of this can get quite involved, being able to anchor the boat very close to an underwater cliff on some south Pacific island that juts straight up from the ocean floor, for example.
Learning about the stars, moon, and tides is very helpful. Tides are absolutely essential because they have such an influence over the boat when it is near port. Some would argue that knowing about the stars and their positions and movements in the sky isn't as important as it once was because of GPS, but I still think it is a good thing to know about, and celestial navigation is interesting besides.
Living the life
Again, practical skills that you can learn to make it all work. You can learn to wash clothes on a sailboat using nothing but a bucket, a plunger or washboard, soap, etc, all it takes is practice, time, and energy. You can cook, sounds like you already know how to do that for the most part, but you might not be used to using the ingredients you will be limited to if you don't have refrigeration - powdered milk, dry ingredients that store well, lots of seeds (wheat, corn, beans, etc), canned goods, but you can forget about steaks and fresh chicken unless you are in port. Living the life is something you can start doing before you ever get the boat, you can just limit your cooking at home to the things you would have available on the boat, for example. Anyway, the point is, you can learn it.
Other general and useful skills include being able to swim, free dive, fish, etc, and most of that is again learned through experience. The boat is on the water, so it is obviously useful to be able to dive under the boat to take care of a few things, and most of the food is in the water so it is nice to be able to take it out of the water and put it over a fire! Learning about the weather is also very important, using weather instruments to predict changing conditions, etc.
Finally, Sailboat design ...
Here I think is where you're going to hit trouble, and I think it is what davidpm and some others were trying to get at. This really is complicated and is all about weather helm, boat balance, and all kinds of other stuff that takes a while to learn and that us newbies can only understand in theory. You don't have enough experience to evaluate whether a design is good or not except to know in very general terms such as whether it has a full keel or not, or what kind of rig it has. We (both of us) are not experienced enough to really know what features of a sailboats designs are important for what we want to do, so unfortunately (?) we simple have to listen to more experienced voices on this point and make the gamble. Sounds like that is what you were getting at when you said you had narrowed the boats down, but it doesn't sound like many of the experienced voices who know really came out and told you which ones were their favorites and why. Wish you luck!