I don't mean to be disrespectful of anybody who has posted to this inquiry, but much of this thread seems to be much to-do about nothing.
Any boat someone chooses as a "starter" boat will be a compromise, unless the buyer has unlimited financial resources. In my mind, there are two basic ways to approach owning a boat.
1. I want to sail
2. I want to own a boat
They're not necessarily the same thing.
We started sailing Lake Michigan out of South Haven Mi 25 years ago on a Catalina 22 with a wing keel. Cat 22 is a great boat to learn on. We made lots of mistakes, sailed in weather that was over our head, etc, but learned to sail.
We still sail out of South Haven, and have owned a Potter 19, O'Day 222, and now a Hunter 26. Certainly none are blue water boats, but were/are suitable for the big lake, with appropriate caution and common sense. I am not interested in sailing across the lake, but we do cruise within 10 - 12 miles or so of shore.
We have seen some awe inspiring weather in our 25 years of sailing. Michigan is not a body of water to be trifled with. Pop-up Summer thunderstorms can bring sudden winds of 25 - 40 knots, and waves of 6 - 8 feet are not uncommon.
My advice would be to set a dollar amount yo are willing to spend on the purchase, and an amount you would be willing to spend on re-conditioning and updating, and but buy the most boat you can comfortably afford. However, don't rule out boats in the 25 - 30 range. Just make sure part of your resources are spent on safety (dependable radio, dependable motor, quality life jackets, solid lifelines. roller furling, etc) and go out and sail when conditions permit.
Be sensible and conservative, and have a ball!