The best way to learn how to sail is on a dinghy. You'll learn more about boat handling, sail trim, the effects of moving weight around, et cetera, on a 13 or 14 foot sloop-rigged centerboard boat in a few weeks than you can pick up in months (or even years) on a larger ballasted boat. For $500 to $1000 you could get the boat, trailer, and maybe even a little outboard (although that probably wouldn't be necessary) and get on the water. Once you're comfortable with actually sailing, THEN you'll know a lot more about what to look for when you start shopping for a boat big enough to live on.
Never forget them. Do something to prevent it from happening again.
Charlotte Bacon, Daniel Barden, Rachel Davino, Olivia Josephine Gay, Ana M. Marquez-Greene, Dylan Hockley, Dawn Hochsprung, Madeleine F. Hsu, Catherine V. Hubbard, Chase Kowalski, Jesse Lewis, James Mattioli , Grace McDonnell, Anne Marie Murphy, Emilie Parker, Jack Pinto, Noah Pozner, Caroline Previdi, Jessica Rekos, Avielle Richman, Lauren Rousseau, Mary Sherlach, Victoria Soto, Benjamin Wheeler, Allison N. Wyatt