My two cents…

MCO question - unless you know you want a wide body at some point, I’d stay with SWA. Better work rules at SWA in terms of flexibility to work and earn versus drop and have time off. (Unless UALs next contract hits a homerun for work rules, then it changes the calculus)

ORD question - unless you know all you ever want is 737 and are closer to Midway, I’d jump to UAL. So much progression coming.

Good luck to both of you