Depends on the goal:
- If your goal is to become a
racer, dingy makes sense as it accelerates the
learning process and teaches subtelties.
- If your goal is to become a cruiser, especially if there is a partner who is less sure about the whole thing, a big
boat makes more sense. Dunking a reluctant spouse a few times when the dingy flips is a great way to kill the dream. Most cruisers aren't constantly tweaking the
sails. You need a basic understanding of how it works and how to do it safely. After that you can refine your skills if you feel the need for greater performance.