One option you might consider before making a substantial capital investment with no real experience is to crew on someone's boat for a season. The chicago area is full of YCs where you can find a boat on which to crew during the racing
season where you'll get some invaluable experience and develop lots of sailing friends from whom you can get some reliable advice from people you know rather than over the internet
Aside from the sailing experience, you'll quickly learn what it takes to maintain a boat which can be a real epiphany to the uninitiated. And then there are the op expenses.