Everyone above is right. Meaning it depends on your learning style. Some folks can get immersed and make the "connections" between disparate boat sizes and purposes, some can't. they all learn, though, whether through lessons or the school of hard knocks. But I do believe the best sailors come out of small, twitchy, less-forgiving boats. Whether those folks become the best cruisers is debatable, though they really have the sailing skills. If they lack the patience, you may find them out racing instead.
I teach 101 part-time, in hot little swing-keel skiffs, and when the breeze is right, we will sail all the way into the slip singing, "Motor? We don' need no steeenkin' *motor*!" Other times we are grateful for the steenkin motor.
103 is more like adding provisioning, camping, picnicing,orienteering, and weatherbird skills to your sailing skills (some people are already good at this stuff--what were your hobbies ashore?). Also in learning about interia (big boats have more), prop walk, anchoring, troubleshooting, jury-rigging, and just being adaptable. Oh, and learn rowing too--they may not teach it, but if you look perfect picking up that mooring under sail, you don't want to look doofusy rowing the dinghy ashore. Plus, it's good exercise when you can't use your bike, gym, or running shoes during a cruise.
I teach 101 part-time, in hot little swing-keel skiffs, and when the breeze is right, we will sail all the way into the slip singing, "Motor? We don' need no steeenkin' *motor*!" Other times we are grateful for the steenkin motor.
103 is more like adding provisioning, camping, picnicing,orienteering, and weatherbird skills to your sailing skills (some people are already good at this stuff--what were your hobbies ashore?). Also in learning about interia (big boats have more), prop walk, anchoring, troubleshooting, jury-rigging, and just being adaptable. Oh, and learn rowing too--they may not teach it, but if you look perfect picking up that mooring under sail, you don't want to look doofusy rowing the dinghy ashore. Plus, it's good exercise when you can't use your bike, gym, or running shoes during a cruise.