Well, I will put in something for FL. You could teach during the year in Florida. Lord knows, they need decent teachers down here and I suppose everywhere else come to think of it. You can ride year round in FL. You would want to be a little careful about where you go, some places have much much better cycling then others.
The thing is that since you are from Michigan you could potentially live in FL for the school year and escape the dreadful FL summer and go to Michigan for their cycling season. I lived in Michigan for a number of years and Michigan's summer cycling season is awfully hard to beat.