We’ve been loyal to Jetblue for our NYC area to MCO flights. Over 10yrs now.
The Jetblue credit card perks play a big part. Automatically it includes 50lb checked luggage for up to 4ppl (even if not using the card to pay for flight - the system recognizes you as a cardholder and automatically removes checked fees for your party). That has been great. We started with really good sign-up bonuses, and when booking flights on points those include all of our carryon luggage plus no change fees.
Which airport depends on flight times and pricing. HPN, EWR, JFK, LGA are within similar proximity for us. I ordered them from our most to least convenient. Best prices are usually the opposite order

Though it is nice to have so many options!