What would you do #2 ?

Yeah, they tossed some money at ATA to get a codeshare deal, but what they really wanted was gate space in MDW. The codeshare was kinda bonus (or a price to pay, depending on who you ask). As for why they don't fly to Hawaii, I'd wager they'll fly to Puerto Rico first from FL. They could have a 90-95% load factor EASILY out of FLL and MCO. I'm betting it has to do with some over water certification issues that cost money.

Not saying it IS his goal, but if he wants options then that would provide the most it would seem. That way he could go to SWA if he wants, or Fed Ex, or UPS, or a legacy, or blah blah blah.
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You should see the number of CAs here going to FedEx, SWA, CAL, etc right now. Most of their time is as a lowly regional CA in an RJ. Maybe some Saab time. No huge int'l jet time there. I'm just saying I don't think it's worth the QoL hit and that the TPIC would be a better asset than flying bigger equipment in a lot of cases.
 
SWA to Hawaii:

ETOPS certification is one big fat hairy monster that involves changing the airplane equipment and pilot training. They might not want to spend that kind of money right now.
 
My dad says there are rumors all the time about Hawaii or Puerto Rico. They do have over water certification now. I've been on a few SWA flights that featured FA's demonstrating life vests. I'm not sure if there are different levels of over water certification. I do know they use it to cut time flying up the east coast.
 
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