If you don't come from a sailing background, how do you get started without taking a class? I couldn't imagine figuring out which boat to buy with no prior knownledge of what is good??
Sailing at a basic level is not difficult, nor is finding a boat for a basic level of sailing. In my own case, there were no sailing schools available, and I'm not sure that I could have afforded one in any case. You get a good book on sailing, one that is not too complicated with advanced details, read it over and over, making sure that you understand and commit to memory the items presented. For a basic level and do it yourself, start with a simple boat not too big or complicated and especially not too expensive. Get someone to go with you to assist, a sailor if available, a boater if no sailor, or just someone who is fairly well coordinated. Since you are starting and unexpected things happen, despite what is in the book, pick your first days when there isn't a lot of traffic on the water and when the winds are low. When you make the mistakes, and you will, lots of them, the conditions are mild and you will see what happens without endangering yourself or the boat. Gradually work up to more adventurous sailing as you learn more about yourself and the boat.
When I started, I had 2-3 hours riding as a passenger on a Columbia 24. But I had admired sailboats for a long time and decided that I was going to get into that sport. If one is going sailing, one needs a boat, so I bought a new Venture 24 (McGregor...I hear the groans...The older Ventures were traditional sailboats (not the motor sailer style currently). I did as I said above and its worked out fairly well.
I didn't have too much invested, so if it turned out that I didn't like the sport, I could sell and get most of my money back. And if I liked it, I could think about bigger and finer boats later.
Being a basic sailor is different from being a good sailor. A good sailor will have spent lots of time at it, and there is much to learn. If you have a sailing school and courses available, and can afford them, then that is a good way to learn and become better. How much knowledge you need depends on what level you plan to participate in sailing. Likewise, the level that you plan to participate in will determine what kind and size of boat that is best. And, the amount of money that you can commit to this hobby also must be considered.
Just my opinion, but I think finding the right boat is vastly overstated and lots of would be boaters go through lots of trouble and expense trying to find that right boat. Most sail boats will do fine on a basic level, and you can select a suitable boat (even if you are inexperienced) if you use just a little common sense. And if you start simple, small, and gradual, you will have plenty of time to figure out where you want to go in sailing and what kind of boat you will need. And rest assured that you can do it by yourself. But you can speed up the process if there is a school available, or if you can find an experienced sailor to teach/assist you in the learning process.
And just my opinion, if one jumps in with no experience to sail around the world or to the islands without having spent some time boating prior to attempting this, that person is very foolish. Likewise, buying a bluewater boat for this fantasy trip with no experience is foolish. You can rest assured that the sea can be an unforgiving place in certain conditions.