I think I understand the rules from this thread, but would someone mind checking my situation below - thanks!

Flying SFO-JFK /stopover/ JFK-SJU-PTP (Guadeloupe- destination) then back PTP-SJU-DFW-SFO

When I work on JFK-SJU-PTP AA insists I have to take the last flight out of JFK (a nasty 10pm dep, 2:30am arrival into SJU). The first connecting flight out of SJU to PTP is at 1pm later that day. Since this is more than 4 hours, I guess they are applying the last flight in/first flight out so that SJU is not seen as a stopover.

My question - is there any way I can legally take an earlier departure out of JFK that same day - my time in SJU would be less than 24 hours but greater than 4 hours. I would not be on the last flight in but would be on the first flight out.

Second option - can I somehow manage an earlier departure out of NY by leaving from LGA or EWR either non-stop or via MIA to SJU?

Thanks for the help!