Boats are like airplanes & cars. The smaller ones are more fun to sail/fly/drive. The learning curve skyrockets, as was demonstrated by a couple of 23 24 yr old guys who, on a lark, found a boat on the internet here in Vermont and kept it at our club (they were up from Atlanta.)
While dinghying by, they offered me beer to teach them to sail, and by the end of the season they took their 27 ft sloop from just S of Montreal to Vieques...just E of Puerto Rico. I recommend a more gradual approach, eh?