Originally Posted by
SpammersAreScum
Oh. Well. Then the first question to ask would have been: "How long a connection will AA allow for a check-through, and is EYW an exception to that?"
I
think the answer is 12 hours,
as stated here, as long as it's not overnight. But as noted above I've been wrong before.
Yes AA will check through on connections up to 12 hours, which would be fine if the OP weren't returning to MIA before continuing onward. I think that will be what stops the OP from being able to check the luggage in through his entire itinerary. But he might be able to get them to just check is MIA-DFW-SAT, anb he should ask at check in at MIA.