I grew up sailing on inland lakes a long, long way from saltwater, closer to the Arctic Ocean than the Atlantic or Pacific. I know how to sail, how to take best advantage of wind, blah blah... I'm good at it.
But I had a dream to sail the oceans. It never quit...
The thing was I knew nothing about yachts, diesel engines, what oceans do, anchoring, etc, etc... Go right down the line, I knew nothing about it. I read about it a lot, but that's not the same.
There was only one way to learn for me. Five years ago I bought a boat. Wish it was bigger, but it wasn't. I love it. The learning experience has been wonderful. Spent $26,500. Now I want to sail it away from Thailand. Will have to invest another $10,000, give or take.
No matter what you spend, even 10 times as much, it's still a bargain.