I travel solo, so price differences between flying and driving are not that much for me. It's 900 miles from Baltimore to WDW, and my truck averages about 22mpg on the open highway. 900/22=40.9 gallons of gas. At $2.50, that's about $103 each way, for a round trip gas cost of about $206.
Flying BWI-MCO generally costs me about $150. But I like to round it up to $200. Renting a car for a week usually costs me about $150, but I usually round that up to $200, as well. So basically, my travel costs for flying are about $300-$400, or about $100-$200 more than driving.
That extra $200 buys me nearly two whole days of time at WDW, since the drive each way would take a full day, but flying takes less than 1/3 of a day each way. $200 is a lot of money to me, but I judge my time and exhertion to be worth it.
When I arrive in Orlando after a 14-hour drive, I'm exhausted, sore and stiff from being cooped up in a vehicle for so long. I'm also bored ouot of my gourd by 14 hours of monotonous interstate scenery. "Look, pine trees... Waffle House... South of the Border sign... another Waffle House... more pines..."
When I arrive in Orlando after a 2 hour 10 min flight, I'm a little stiff from the small airplane seat, but far less than after 14 hours in a car. I'm far less tired and bored, since I was a passenger, not a driver, and was able to sleep, read, and listen to music on the plane, and I still have most of the day to enjoy myself in the parks.
Time and money are certainly factors that must be considered when traveling. But there's another concern: aggravation.
Aggravation varies from person to person.
Your example shows that flying aggravates you more than driving. But in my case, the aggravation is far less when I fly than when I drive - and this is also the case for many families with small children.
When I fly from Baltimore to Orlando, I show up at BWI 2 hours before my scheduled take-off time, get through checking bags and passing security fairly quickly, and usually have more than an hour to relax in the terminal, have breakfast, and read something before boarding. I've been fairly lucky with weather and mechanical delays over the years, and never been stuck on the tarmac. I also fly non-stop, so I never have to worry about changing planes or dashing across an airport to make a connection - I am willing to pay more for non-stop.
From the time I leave my apartment, my total travel time to WDW when flying is about 6 hours - 1 hour drive to BWI, 2 hours wait/boarding time, 2 hours 10 mins flight time, about 20 mins to collect my luggage and pick up my rental car, and about 30 mins to drive to my resort or hotel. I've been quite lucky over the years, and the most I've ever been delayed has been about 3 hours due to mechanical problems with an aircraft.
When I drive to WDW, it takes about 14 hours on the road from door to resort. I drive it straight through, by leaving at about 4am and arriving around 6pm (a few times I've driven overnight, leaving at 6pm and arriving around 8am). But 14 hours on I-95 is boring, monotonous, and uncomfortable, not to mention the stresses I encounter with other drivers trying to kill me, cops trying to ticket me, and gas stations trying to fleece me. And for families with small kids, who can't sit still and quiet for 14 hours in the back seat of the family minivan (they can only watch so many DVDs before they get bored), a 14 hour drive is impossible.
So I fly. Knowing the potential problems of both methods ahead of time, I still prefer flying, because if I compare a perfect flight to a perfect drive, the flight is still far shorter and easier.