It's an admirable plan, but the amount of time you'll have to invest in planning your commutes will put a damper on things. I commuted one leg to a regional for 9 years almost exclusively to one base. I knew the flight schedules by heart. You won't have that luxury if you're talking about commuting out of rotating airports. If you do this, I would always be close to an airport that gives you a one leg flight option to work. For every added leg of your commute your stress will increase exponentially.

Good luck and hope you can at least give it a try.