Always present things in a way that will make him think it was his idea!
Flying will put you there in 4-5 hours (I'm guessing - it's a 3 hour flight from CT); driving will mean 2-3 days on each end. Add up the cost of gas, overnight accommodations, food and tolls along the way, and weigh it against the cost of flights. I have also weighed the cost of staying off-property vs. on-property - I figured I'd book the flights, then use a Groupon to save money on an area hotel, but two of the "really nice" ones we liked received horrible reviews. At least at Disney, you KNOW they will make things right.
Disney makes things SO EASY! You get off the airplane and onto the bus and are brought directly to your hotel. Your luggage is brought to your room. The stroller you rented is waiting for you (use a rental agency for a double stroller). Rather than schlep everyone into a hot car, you get on an air conditioned bus that takes you to any of the parks or back to your hotel.
With kids your age, my best advice would be "lower your expectations." Do not alter their schedules (eating, naps) but build the trip around them. Don't expect to see it all or do it all; prioritize the most important. Allears.com has two great articles on "overlooked attractions" that may appeal to kids their age.