I would imagine the peak season to Key West would hurt the commute pretty good. When I was down there all the flights were full.
Listen to these guys about commuting. It really sucks. I have been two sometimes 3 legging it for over a year and a half and finally gave up. I ended up doing 1 leg with a 1:45 drive after. The direct flight is so much easier to work with and I can control my drive vs extra worry with 1 or 2 more flights added on.