I'd fly in a heartbeat.
I'd break it down this way:
1,100 miles each way means about 20 hours of driving. I'd need a hotel to make it work You've got meals each way and tolls.
So, conservatively, It would cost me at least $600 to drive. ($300 gas, $50 tolls, $100 food, $150 hotels)
If I fly, it's $1,000 - $1,100. My cost savings are about $500. To save that, I need to add 40 hours of driving time and aggrivation. That's another 2-4 days tacked onto my vacation (or detracting from my park time).
With all that driving, I'd be worn out and my vacation would probably end up being more stressful.
The flight from BDL to MCO is about 2 hours each way - or 4 hours total. I'd get up, head to the airport and be in the parks the same day as I left.
On any flight to Orlando, there are tons of kids. It will be fine