I won’t tell him that. It will go to his head.
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Good plan. The only thing worse than being married to a genius, is being married to an ARROGANT genius.
(Just ask my wife!) 
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We (family of four) fly Southwest all the time and have never used their Early Bird option. I just make sure we check in at 24 hours and even when we get mid C numbers, we’ve always been able to sit 2 and 2 in nearby rows (almost always in front of each other).
I really wouldn’t stress over it.
If you plan on using anything other that traditional WDW transportation, I would have each kid bring a low back booster (LBB) seat on the plane (everyone gets a carry on and personal item, the LBB fits within the size guidelines and easily slides under the airplane seat). Both of my kids easily carried their own LBB seats along w/ a backpack through the airport.
You can also check out the Bumble Bum booster. We used one when my ds was around 10yo during a trip to NYC. It was a great option for using a booster on the run. The seat is really lightweight, comes in a travel bag, and blows up/deflates in about 1-2 minutes. [Note that I was a car seat technician for 14+ years so I have a pretty high threshold when it comes to making sure seats are used correctly.]
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Agree with @minniemouse27. We fly SW frequently to Orlando and have been for years. We never purchase early check in. We check in right at 24 hrs. Even when my kids were too old for family boarding, we have managed to sit together. I wouldn’t worry.
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Thanks all. This has been informative and reassuring (and a bit amusing 
)
We love Southwest. However, we have had it happen where we have paid for the Early Bird option but because our flight was apparently a continuation of another puddle-jumper flight most of the seats were already taken which made the early bird worthless.
Early bird doesn’t guarantee an early boarding position it just means you don’t have to check in and you can board before people who aren’t business class/A-list and didn’t purchase early bird as well. I’ve read stories of people getting early bird and getting C boarding.
That’s awful. I would be upset.
I agree with @ryan1 Driving is a good option. I’m from NJ and just go down I95 for the most part then I4 west. I try to leave at night after rush hour. I can drive round trip for around $600 or less, that includes gas, tolls and hotel.
FYI, booster and car seats don’t need to count against your luggage allowance! They fly for free or the kids can just use them in the seat.
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We always fly SWA to Orlando for Disney trips, and have had really good luck! We’ve done early bird before (and gotten early A each time), and when kids were younger we did the family boarding they offer if you have younger kids w/ you, it’s after A group, but before B group, so that’s an option as well. As for the early bird, you can add to your flight anytime until a couple days before I believe, BUT the earlier you add it, the earlier you’re checked in at that 36 hour mark. A SWA agent told me they go at 36 hours in order of EB purchased…
They can use a harnessed car seat, a belt positioning booster seat (low or high back) cannot be used on the plane…the low back booster can be carried on and fit under the seat.
If you carry on a low back booster, be prepared to repeat over and over to the flight attendants that you have no intention of using it on the plane. <— I know this from personal experience!
That’s my understanding as well. The earlier you purchase EB, the earlier you will be checked in. If you wait to the last minute, you may not get much of an advantage out of it.
Our main reason for purchasing was that on the return portion of our trip, we were on a cruise ship and I didn’t think we’d be able to easily check in online at the 24 hr mark.
I got something ridiculous like b-45 after paying for it once on a business trip.