The fly vs. drive question is one I constantly struggle with.
On one hand, I can book a Southwest flight in advance for around $150 round trip. This isn't bad at all and since I'm currently preparing for just myself (although that could change if I find the right person).
With driving, I can make it from Pittsburgh to Orlando in about 16-17 hours, assuming I stop for some stretch breaks and eat the food I've packed. I'd likely also stop halfway at a grocery store to get some stuff for the trip with the intent of eating some meals in the hotel and getting snacks which aren't easily purchased at WDW (namely fresh produce and skim milk). For me, this is a one-day drive, although I'm likely going to crash at the hotel that night.
Factoring in gas, we're looking at maybe $150-175 total, round trip, assuming I don't use the car much or at all at WDW. However, having the car makes it far easier to go to a resort to eat if I'm not staying there.
Then there are the questions of convenience...
• Do I really want to drive a total of 38 hours round trip vs sitting in a plane for 5 hours round trip?
• Do I really need the car at WDW?
• Is the extra 33 hours worth it for the sake of having the convenience of a car I don't have to rent?
• How important is it to get groceries at a place that doesn't price gouge?
• How much am I planning to buy souvenir-wise at WDW?
That last question is the biggie for me. My suitcase is big enough to accommodate a lot of purchases, but let's say I get some fragile stuff--we'll say some Christmas ornaments, mugs, dishes, etc. Let's also throw in something larger size. Last time, I bought a Hollywood Tower Hotel robe. Those aren't exactly small--folded up, it takes up as much space as a typical laptop bag.
I'm not too concerned about the luggage that I'm taking, it's the luggage I may bring back. I know there are some people who have perfected the art of putting these things into suitcases, but I'm not one of them. I have a degree in education with a minor in psychology, not a degree in shipping with a minor in fragile objects. I don't really want to pay to have things shipped, either. Part of me is thinking of taking a relatively empty carry-on and using that on the airplane on the ride back, plus if I buy something like a robe or towel (believe me, I have more Hollywood Tower Hotel stuff than you can shake a stick at) it can serve as packing material.