Fuel contract with 2 planes will just be tearing up money. How much & what % discount is contract, and how much is your weekly fuel bill?
Also, you're flying 5 daily flights to 4 different airports, instead of all to 1 airport. Looks like BDL-MCO takes almost exactly 8 hours per round trip with an MD90, and it can easily accomodate 9 daily flights. So start with 3 MD90s, all flying 3 times daily to MCO, and you won't be wasting money on staff & marketing costs.