Having flown this route more times than I am willing to admit in public, here are my opinions of the carriers I have used, in order from "Best" to "Worst":
American - San Jose use to be (and to some extent still is) a mini-hub for AA. Because of this, they are located in the "newer" Terminal A. The best connections are in the morning, when they connect through Dallas-Ft Worth or Los Angeles (with Non-Stop LAX-MCO). However, the evening flights seem to be limited to connections through Chicago (ORD) or Boston (BOS), neither of which have the best reputation during the winter months.
United - This would be my favorite except they are located in the older Terminal C and all boarding is outdoors and up stair ramp to the planes. Choices are SJC-LAX-MCO and SJC-ORD-MCO again, plus another route that can connect through Washigton-Dulles (IAD - another wintertime question mark). Morning flights take you though their Denver hub.
Delta - Only flew Delta once and don't remember anything good or bad. Another Terminal C /outdoor boarder but the connections through Atlanta (ATL) look like the best for what you need: good conncting cities at red-eye hours.
TWA - I flew TWA for the first and LAST time this Easter. They had a decent fare through Lowestfares.com so I thought I'd give them a try. Big Mistake! They were going through a Bankruptcy and negotiating a buy-out by American. Service was terrible. THere was no Curbside Baggage in San Jose and very slow skycaps in Orlando. Check-in was the slowest I've ever encountered in my life. And the food service was horrible, meals were frozen by the refrigeration system, but they handed them out anyway (YUCK!).
Sorry about the length. All said and done, your first choice of Delta is probably the way to go for your red-eye schedule.
Steve
