[beefield]

> but given my location, I don't want to put money into it

You made me a bit curious, why not? Illinois seems to have sailing opportunities in many places, and with a good drysuit or wetsuit even dinghy sailing in colder climates is fine. And if you still do not fancy swimming, there are small keelboats you can handle on your own relatively easily. (Take your time to learn in easy winds and preferably a teacher of some sort, though)