I have a very unique perspective on this specific topic - let me explain...
I drive thousands of miles for work every year - so far since the 3rd week of September I think I'm over 5,000 miles now. (I'll actually know on Friday when I return my rental car
) 
So vacation for me involves very little driving or a road trip style seeing tons of stuff along the way. Marathon trip bore me to death now - I make them so often for work, doing it on vacation is of no interest to me!
So before I go further let me do a quick run down of our trips and transportation -
Drive time is 16-17 hours from where we live to WDW.
Flight time (actual time in the air is around 2 hours)
October 2006 - (Honeymoon Trip) by air
September of 2008 - By air
January of 2009 - By air
December of 2009 - Drove straight through (stopping for naps/meals/gas etc) left at 11:00pm and arrived around 4:00 the next day.
May 2010 - Drove 1/2 way (to visit family friends) then finished up from Noon-9:30pm next day.
September 2010 - By air (short trip - got really cheap airfare)
OK - so that covers all of our trips so far.
Driving so much for work, I really don't like to drive - but flying isn't my wife's favorite thing - so we have to balance it out some (well, we've started to! LOL)
OK - so we are getting ready to take our next trip - and it's from a different starting location - we won't be home when we start this trip. Since we check in on the Saturday after Thanksgiving and we are spending Thanksgiving with DW's family 5 1/2 hours from where we live - the trip would have been almost 20 hours - and to that, I said a big NO WAY!
So - what are we doing this time?
The AUTO TRAIN!
We took our first train trip last year from Baltimore to Boston just because we had always wanted to take the train! We had a really positive experience and found it to be a great - less stress - alternative to flying and a less boring/tiring alternative to driving.
So we will drive from DW's family's house in PA to Lorton, VA on the day after Thanksgiving - and board the train, leaving VA around 4:00 or so. We are scheduled to be in Sanford, FL by 9:30 the following morning.
First off we are avoiding all the interstate traffic, second we will arrive we rested as we booked a sleeping compartment, AND we will arrive there WITH our car, and all the luggage that we want to take - packed in our car - with no worry about the hassle of airports, checking bags, arranging transportation, or anything else that would just make it to be a horrible trip!
SO - would I consider driving your distance - NO I would not, it's just too far especially if you have a family or if you are limited on your number of vacation days.
We have had good experiences driving - but it still isn't my favorite thing to do, it's very stressful, my wife doesn't drive much on long trips and she hates to drive after dark - and for me - it's hard to stop at a hotel to sleep when I know that I could be driving - getting closer to our destination.
Plus once again - back to my work situation, I HATE getting luggage out of the car KNOWING that I will just be putting it right back in the car the next morning. I hate packing and I hate unpacking! SO I like to pack and unpack once on either end of trip - UNLESS I'm staying for a few days.
Anyway - that's us - that's how we travel.
Your cost goes up when you drive considering the need for a hotel, meals, fuel, and by chance any vehicle repair problems you have (but still understanding the OP's situation not having to cover any of the vehicle expenses) I wouldn't drive that distance unless it was a 2 week or more road trip with some 1+ day destinations in the trip there and back.
But then again - I'm jaded on rushed driving trips - and I'm a fan of enjoying the journey!
So while some people would 'never' drive - others would 'never' fly.
But when you make the decision one way or the other - do it calculating all cost - even the cost of taking extra days off!
I drive thousands of miles for work every year - so far since the 3rd week of September I think I'm over 5,000 miles now. (I'll actually know on Friday when I return my rental car


So vacation for me involves very little driving or a road trip style seeing tons of stuff along the way. Marathon trip bore me to death now - I make them so often for work, doing it on vacation is of no interest to me!
So before I go further let me do a quick run down of our trips and transportation -
Drive time is 16-17 hours from where we live to WDW.
Flight time (actual time in the air is around 2 hours)
October 2006 - (Honeymoon Trip) by air
September of 2008 - By air
January of 2009 - By air
December of 2009 - Drove straight through (stopping for naps/meals/gas etc) left at 11:00pm and arrived around 4:00 the next day.
May 2010 - Drove 1/2 way (to visit family friends) then finished up from Noon-9:30pm next day.
September 2010 - By air (short trip - got really cheap airfare)
OK - so that covers all of our trips so far.
Driving so much for work, I really don't like to drive - but flying isn't my wife's favorite thing - so we have to balance it out some (well, we've started to! LOL)
OK - so we are getting ready to take our next trip - and it's from a different starting location - we won't be home when we start this trip. Since we check in on the Saturday after Thanksgiving and we are spending Thanksgiving with DW's family 5 1/2 hours from where we live - the trip would have been almost 20 hours - and to that, I said a big NO WAY!
So - what are we doing this time?
The AUTO TRAIN!
We took our first train trip last year from Baltimore to Boston just because we had always wanted to take the train! We had a really positive experience and found it to be a great - less stress - alternative to flying and a less boring/tiring alternative to driving.
So we will drive from DW's family's house in PA to Lorton, VA on the day after Thanksgiving - and board the train, leaving VA around 4:00 or so. We are scheduled to be in Sanford, FL by 9:30 the following morning.
First off we are avoiding all the interstate traffic, second we will arrive we rested as we booked a sleeping compartment, AND we will arrive there WITH our car, and all the luggage that we want to take - packed in our car - with no worry about the hassle of airports, checking bags, arranging transportation, or anything else that would just make it to be a horrible trip!
SO - would I consider driving your distance - NO I would not, it's just too far especially if you have a family or if you are limited on your number of vacation days.
We have had good experiences driving - but it still isn't my favorite thing to do, it's very stressful, my wife doesn't drive much on long trips and she hates to drive after dark - and for me - it's hard to stop at a hotel to sleep when I know that I could be driving - getting closer to our destination.
Plus once again - back to my work situation, I HATE getting luggage out of the car KNOWING that I will just be putting it right back in the car the next morning. I hate packing and I hate unpacking! SO I like to pack and unpack once on either end of trip - UNLESS I'm staying for a few days.
Anyway - that's us - that's how we travel.
Your cost goes up when you drive considering the need for a hotel, meals, fuel, and by chance any vehicle repair problems you have (but still understanding the OP's situation not having to cover any of the vehicle expenses) I wouldn't drive that distance unless it was a 2 week or more road trip with some 1+ day destinations in the trip there and back.
But then again - I'm jaded on rushed driving trips - and I'm a fan of enjoying the journey!
So while some people would 'never' drive - others would 'never' fly.
But when you make the decision one way or the other - do it calculating all cost - even the cost of taking extra days off!