Kansas is much too far from real water, No doubt!
Here is a suggestion that would make sailing in spectacular places easily accomplished given your family and employment situation. Consider New England. The Carib is just a nice cruise away or a flight to charter anywhere you choose for a couple of weeks. That would be very possible during winter months when your boat is safe on the hard. Great cruising grounds, excellent cruising weather (not life threatening sunshine every day but fair winds and plenty of places to hide if necessary), a maritime culture with lots of possibilities for where you locate. Cities like Boston or Portland, (my Maine bias) are full of life and opportunities. The inland country is varied and spectacular. Mountains, rivers, lakes, wildlife,......Great hospitals and schools. Small towns too. My GP built his own 34' aluminum ketch here in Bar Harbor. Sailing? Sailing is done all day, every day from May to October. The Maritimes offer Canada's hospitality for summer cruising. The Maine coast could take you the rest of your life to explore and if racing is on your mind, that too.
I'm just saying! It is our little secret