Re: New to sailing
I started sailing about 6 years ago, and I took 4-5 days of lessons in Chicago and then 4 days of lessons on larger boats in Duluth, and bought my boat (Ranger 26) the day after I finished the lessons.
I was super cautious the first summer, but everything worked out really well. Now I live aboard the whole summer, cruising the Apostle Islands and anchoring out for weeks at a time.
I think a combination of a few lessons and a reasonable boat can be worked our surprisingly quickly.
Good Luck to You, Gregg