Depends on where your flight is coming from - and if it leaves on time. I know from NYC unless there is some major delay or we have to reroute for some reason (coughMarALagocough) we almost always land 20-30 minutes early.
Granted, I don’t fly Southwest (they screwed me over one too many times), but I wouldn’t count on Early Bird necessarily having you right up front - especially going to Orlando. I have friends who do fly it, got early bird, and were still at the back of A/start of B because so many people going to Orlando buy it.
I personally wouldn’t use a car service that didn’t answer all the other questions you have. The ones I would consider ask for the flight informatoin and THEY monitor the arrival. As for their cancellation policy, if you can’t find it on their website (BIG RED FLAG if you ask me), I’d call them and ask. And if there’s not a phone number, I’d use a different car service.