Chapman Piloting & Seamanship 67th Edition (Chapman Piloting, Seamanship and Small Boat Handling) This book is quite comprehensive.
The One-Minute Guide to the Nautical Rules of the Road, A United States Power Sqaudrons Guide. This book explains the rules and I find it easier to remember them with an explanation
Take the American Sailing Association courses 101, 103 104: Advanced Sail Training Courses - Endorsements from American Sailing Association
With these books and classes
, I found I knew more than the folks at the little yacht club I belonged to for a year. Cost was $325/year. This gave me a place to store the sailboat on its trailer and I could leave the mast
up saving an hour and a half per day getting the mast
up the beginning of the day and backdown at the end of the day. If you go with the trailerable sailboat, get one with a keel
that has weight in it unless you are sure you can get the boat righted if the sailboat tips over. If you go with a centerboard
type where you move from one side of the boat to the other when you change tack or direction, you will eventually have to get it right side up and bail it out if you catch the wind
sailboats are smaller than keel
boats. There are also sailboats with moveable keels (up and down) that are easy to put on a trailer
You may want to get The Sailor's Book of Small Cruising Sailboats by Steve Henkel. He describes 360 sailboats under 26 feet. The only problem with his descriptions is he thinks inside volume is everything; however, sailboats a compromise. If you want a sailboat that is good in a storm, his criteria might not be the best.