I was convinced that I only wanted to fly from Memphis to Orlando until Delta jacked up flights to over $400! So I fell in love with driving.
I do have a good amount of vacation time each year so have the luxury of taking a rest day when I get home. If that weren't the case, I would try to fly more often.
And I love having a car at WDW. I take a big cooler full of groceries, a case of water, snacks, sodas - all sorts of things. Because I have that stuff with me, I don't feel as if I have to stop at an unfamiliar grocery store, which would not be a magical experience for me. This means I can have more meals in the room which also saves money.
Right now I am experimenting with driving strategies. It's about a 13 hour [including losing an hour for EST] drive from Memphis. The last few times, I've left super early [4-5 am] and gotten to WDW by 6 pm at the latest which means I spent my first nights either sleepwalking through the parks with friends who had already flown in or camped out in my room, wishing I had enough energy to go to the parks.
This time I will be stopping about 80 miles away - found a great deal on a cheap place to stay. Hopefully, this will give me a full night's sleep and I'll be ready to tackle WDW the next day - woo-hoo!
About being cooped up with your mom - I can completely understand. Audiobooks have become my favorite traveling companions. Your local library probably has a good selection that would appeal to all three of you. It's a great way to pass the time and you don't have to fight over the radio.
Go for it!
Edited to add: Ha, just saw on another thread that you got a great deal on Air Tran tickets - yay, you!!!