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To some extent, the answer to this question depends on your own personal goals. We each decide how skilled a sailor that we want to become. Some simply want to learn just enough get in and out of the slip and make simple passages, while others of us feel that it is important to highly develop sail trim and boat handling skills. Most fall somewhere in between; there is no one right or one wrong answer to this.
Having taught a large number of people to sail in my life on all kinds of boats, I can tell you that it is much easier to learn to sail on a responsive, comparatively small (under 30 feet) and comparatively lightweight, fin keel spade rudder sloop. Boats like these 'talk' more directly to the novice sailor helping them feel what is happening when they make steering or sail adjustments.
When you talk about a a poorer sailing boat like the Cheoy Lee Luders designed ketches, it is much harder to develop sailing skills because there is very little feel, very little indication when you are doing the right thing of the wrong. In moderate winds this does not matter all that much, but when sailing at the lighter end or heavier end of wind range the inability to properly adjust the sails make a huge difference.
The Great Lakes are notorious for light air punctuated by extremely heavy conditions. Sailing a ketch in these changeable conditions can be very frustrating to a novice who is slower to make the right adjustment on the fly.
Small ketches for all of their charm are not an expecially good choice for a novice sailor, especially in your sailing venue. Because of the interaction of the windward sails on leeward ones, ketches are much harder to trim well. Most experienced sailors can make sail adjustments that are roughly right. The loss in speed, comfort, and ease of handling are not all that significant if you don't mind going a little slower and motoring a bit more. But getting the sails trimmed right, and keeping the boat moving can be an exercise in frustration for a novice.
Jeff
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