Welcome! I grew up in Omaha, so I know that the opportunities for sailing are pretty limited around there. On the other hand, that's where I first learned to sail, and I honestly think that learning
to sail on Lasers, Hobie Cats, and dinghies makes you a better sailor in the long run.
As an example (and we see postings here virtually every week about this), a lot of people who only learned on larger boats get really nervous as the boat heels. Well, if you've sailed on boats where half the fun is seeing how far you can heel it over before it tips, then you can only shake your head
in wonderment at such people. A sailboat is SUPPOSED to heel over! That's not a problem, that's just sailing. When you've "been there, done that" you realize that it is pretty easy to tell the difference between a boat that is heeling normally in a stiff breeze, and one that is getting close to going onto its side.
And spinnakers. I am amazed at how many cruisers not only do not use one, but are really adamantly opposed to even trying. They think they are too complicated. Too difficult to use. Not worth all of the time and effort. Well, again, when you learned on boats where pulling out the spinnaker
was a normal thing that just made downwind sailing that much more fun, then you know how silly the fears of so many sailors are. Flying a chute on a 35' boat really isn't that much more difficult than flying one on a Laser, and the benefits are SOOOOOOO worth it!
So, my first bit of advice would be to take advantage of the sailing opportunities that you do have. Learn how to trim a sail, how to fly a chute, and how to adjust the rigging
. These are all skills that are pretty simple to perfect on small boats, and will serve you extremely well when you move to larger boats.
Then, search around. There are a few good sized lakes in the area where it wouldn't surprise me to find boats in the 25-30 foot range. You might find some racing
clubs with skippers who would welcome a hand during their club races.
If you can afford the occasional long weekend then I know there is a club in Denver, at Cherry Creek reservoir, that sails
J22s and J24s. There is also company that runs ASA
certified sailing classes
there... Welcome Aboard !!
And, of course, Chicago is only a long days drive from Omaha, and I would be shocked if you couldn't find a certified sailing school