Re: Ideas and/or guidance
From Kansas you should really look at Great Lakes sailing. Travel there will be greatly simpified. I've been supscribing to "Good Old Boat" for a while and they (the editors) are Great Lakes sailors. Their season is just about four months, locales are spectacular, weather pleasantly cool in the summer (they seem to think 85 degrees is a broiler) and sailing grounds unlimited, especially for someone with four full months to sail.
You could then augment your summer sails with a charter in the tropics, and do you have ice boats in Kansas?
I'll bet that if you contacted Karen Larsen and Jerry Powlas at good old boat they would give you a very picture of what to expect.