Welcome aboard Lance.
I'd suggest you try these avenues to see if this might work for you?
US Sail program or the American Sail Association program. They both are about the same content and internationally regognized.
I know a little about the ASA
courses. The ASA program would start with 2 keel
boat classes that cover sailing in general. Then the 3rd course would be "bare boat chartering". It covers a few sailing items but mostly cruising boat marine
The idea is you have to know how to operate everything and what everything does and practices you have to understand to operate a boat other than just sailing.
The other option would be to travel to a marina. And ask around and talk to different sailboat owners. Try to become friends with one or two of them?
Now about boats. I'd recommend something like a sailing dinghy
. If you're going to do it alone without any schooling!! These kind of boats a re very small. And not as expensive as your bigger boats. After you honed your skills, you could move on up to a bigger boat. Like a Catalina
27 or bigger. Depending on how comfortable your sailing skills are.
Whatever you do. Even after you learned your sailing skills. Do not buy a boat bigger than 40 feet long. After 40 feet, they get harder to handle single
handed. Also, any boat longer than 40 feet starts to double in price
per footage. Or something like that.
Just take it in steps. Learn as much as you can from a school. And look into these two weblinks. They might provide the necessary training you are looking for.
Most of all from me. I wish you the best of luck!!