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Discussion Starter #1 (Edited)
Ladies and Gentlemen,

Hello from Chicago!

I just tonight received my US Sailing Basic Keelboat Certification from Chicago Sailing out of Belmont Harbor Dock B. 32 total hours combined on the water on J22's, J30's and a Tartan T-10, followed by the US Sailing 80 question written test. I only got 3 questions on the test wrong, and you are apparently allowed up to 20 incorrect questions to still pass the certification. I am very excited.

Growing up in the North 'burbs, we went to Door County 15 or 16 summer's, where we would sail, pontoon boat, and ride my Uncle's jet boat and later cigarette boat.

I fell away from boating for years, but was re-inspired after a good friend of mine and I bicycled to the lakefront to watch the America's Cup. On the way to the lakefront, we rode down the river and I couldn't help but notice all the very happy faces of folks on boats on the river.

Although I don't make lots of money, it occurred to me that I have lived downtown for 17 years and never taken advantage of the lake for boating because it always otherwise seemed like something only the wealthy could do.

Watching those sailboats, I remembered that sailing is a nice way to enjoy boating without spending a fortune on gasoline.

I signed up for Chicago Sailing's Basic course the very next day. Upon completion, I signed up for their Advanced course which was offered a month later.

I have been scouring Sailboatlistings.com and keep coming across Pearson 26s, Hunter 25.5s, Catalina 22s, Cal 27s, etc., for around $3500-$4000.

I am a handy dude as I do almost all the maintenance to both my street and my racing motorcycle. I am not afraid of a challenge, whether it be diagnosing and then fixing diesel engines (which I currently know nothing about) or sanding and refinishing teak. I am ready to learn and look forward to the challenge and ultimately the reward of fixing up an old boat.

I plan to purchase before the coming season, March or April of 2017.

I have deduced that I want a tiller, in-board, marine head, sink, and stove. I intend to sail single-handedly once or twice per week, and then frequently on the weekends with my wife/family/friends when not at the motorcycle track. I am also very interested in weekend trips to Milwaukee or Indiana, hence a ~25' or so boat with a head and a stove for reheating food and coffee in the mornings.

If I seem off-base or have a little too much bravado, let me know! I am here to learn how to do it best prior to purchasing in early Spring. Or please share with me any experiences of buying your first $3000-$4000 boat and all the headaches/good times/explosions, etc. :)
 
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