Slappette and I have gone to WDW together 5 times (we live in central/southish NJ). 1st time we flew down, but had to drive our rental car back because a hurricane was coming and the airports AND the parks were closed. We drove to the Alamo lot at the Philly airport, stopping for food and bathrooms and the occasional leg stretch in about 20 hours. After that, we drove the next few times, Slappette's not big on flying, and while it certianly takes longer, it's also a little freeing - you're on your schedule, not the airlines', you're not in a tube with recirculated air where one person with the sniffles can cause a flu outbreak by landing, you have your car with you so you don't need a rental, you can pack extra stuff you think you might need without extra baggage fees, and everywhere you go, there's a Cracker Barrel!
Now, I prefer driving straight down - leave in the early evening, do most of te driving at night when traffic's lighter, get there mid-afternoon, do an early dinner and lights out before long so we can hit the ground running the next day. Slappette prefers taking a break and getting a hotel. My only complaint with that is, when I'm in any hotel, it takes me until the second night to get a good night's rest (unless I'm exhausted from driving 20 hours straight through, like I'd like to do to get to WDW
), so that one night in a hotel does me no good at all. I'm jusy antsy to get back on the road, uncomfortable, and therefore I don't sleep.
Mid-December of 08 was the first time we went with our li'l Slapperina (she turned 5 months old during that trip), and it was the first time we tried the AutoTrain. You may remember, 2008 was the year gas prices officially went bat-____*t crazy, with months of prices being over 4 bucks a gallon. We originally considered taking it one-way and driving back, but gas prices at the time I made reservations were crazy enough that we just went whole hog (they wound up going back down before our trip). Slapperina just couldn't deal with driving unless she was asleep, so the idea of only driving when she was sleepy would've resulted in a 3-4 day drive. So we did the 4 hour drive to Lorton VA, she slept through 3 and a quarter hours of it, then screamed like a banshee the last 45 minutes. We had a sleeper car to keep her out of most people's hair if she screamed through the night. Wasn't ideal, but it worked out better than a drive would've on that particular trip.
Next time we go, I've no idea how we'll do it. If Slapperina is still teeny, I'll probably argue for the plane again, so if she's miserable it's only for a few hours, not 20 or more, and it's not like she'll be the only baby on a flight to Orlando
But as far as the drive goes, Slappette and I did it a few times, and it definitely can be done. What I'd suggest is a hope for the best prepare for the worst scenario, have a list of a few hotels you wouldn't mind stopping at along the way if you decide you're too exhausted to make it, and make sure the list includes hotels throughout i-95 so if you decide to stop, wherever that it, you're ready. Many hotels will offer AAA members discounts. Stick with national chains; no guarantees that it'll be an awesome hotel, but the odds are better. Many places will offer at least a free continental breakfast, so it's one less stop you'll need to make in the morning.