Seems like you have gotten a good start with a good day sailor at least it can get you on the water to start learning. I have been a sailor for 20 years off and on and it has always been a huge passion for me, even when i am away from the water. I have been a pilot for 9 years professionally for most of those. When I was a student pilot I hitched a ride on a J92 during a race with a fun crew, turned out the owner was a airplane pilot, helo pilot and A&P for US customs. We became good friends, and both love flying but it is just a job, sailing is a whole lot more fun. It might be different if I got the kind of planes you did.
For the type of sailing you are looking at I would suggest visiting the trailersailor.com website. While the # of people and breadth of experience here is far greater that site is more geared towards the kind of boats and sailing you are looking to do. I know at least two people from there live in IN.
You will be surprised at the number of sailors around everywhere. If you can hook up with someone you could get a few lessons, get some books and teach yourself to sail. Once you get a bigger boat you can then take a class to learn to reef, dock and anchor the boat which is where it gets trickier when you are learning.
If you do not live near the water fix up and keep the dingy for short little day excursions, also they can be a lot more fun just to get out when the wind is right. For a bigger boat I would suggest a Catalina 25, much better sailor than a Mcgregor. Seems like the best all around boat for the money. Decent performance, decent build, very good space below for a boat this size. Most anything in this size will need at least a 1/2 ton pickup this will need a 3/4 ton for this one.
We are looking at two fin keel C25s ready to sail for $5-6K. You could buy a boat like this and a truck with your budget. In your price range you should look at the 88-89 wing keel as they are best equipped and sit low on the trailer and are easier to launch. In the mean time enjoy the dingy sailing.
West Wight Potter 14 "Lemon Drop"
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