I can tell you how I got started, which might help.
I started on Lake Michigan in a small inexpensive boat - a Hobbie Cat - I know you are all laughing now - but it was a great experience - close to the water, hiking out and if you have another heavier crew member with you, if you turn it over because you've just gotten to crazy in stiff wind, you can always right it. It gives you a good feel of when you are on the edge.
I then started branching out. There were several sailing schools around so I took a course with an old salt who had sailed around the world once. I rented a boat. I had like an 1/8 share and got to take the boat only on certain days. It was about a 40 footer. At the same time I started taking courses at the local planetarium. I took a course on navigation stars, another on plotting your course with dead reckoning and drift considerations, another on navigating with a sectant and I practiced. I read a couple of books, at the same time I was sailing, so I had recommendations from experienced sailors on what they had done on their extended voyages.
Alot of the advice was about things I wouldn't have thought of. Like what type of stove is good for tropical living, what fuel is readily available for it in foreign ports, safety wiring bolts with aircraft wire so they don't loosen and get lost in the drink.
Got a 24' racing sailboats so I could do class racing. Racing teaches you a lot. Sometimes you're racing and the weather changes for the worse, but you're already out there so the race isn't cancelled. That means you are pushing the edge and it also means you are learning a lot. You are also comparing your skills - whether you want to or not - with the rest of your competitors. You instantly know when you're not matching up because you'll be left behind. It has other benefits as well. You registered for the race so if anything does go horribly wrong, at least someone has a good idea where you are and that they need to go find you.
Finally I was ready for my dream boat. From reading I knew what equipment to buy, I had been practicing navigation right along, could navigate with a sectant - which I had to do because at the time GPS didn't cover the areas I was sailing - and knew what to do in heavy weather.
Hope that helps.