We spent several years thinking about this possibility. Our last trip was a three week stay and that was more Disney than we wanted. Though we've been
DVC since 1996, AP at the time and had purchased quite a few contracts anticipating this situation we decided against it.
We'd have to drive (even bought a car for this) 24+ hours from NH. DH is sick of heavy traffic and road rage and I agree. We would have to stop twice (once was to be HHI) both ways. Gas/hotels/tolls etc was not a factor.
Prices have gone sky high at WDW and quality has gone way down. 10K a week doesn't seem worth it to us anymore...40K not happening. Our son and DIL are factored into that amount at 10 nights a year.
Instead, we decided to build a new home where we can relax and vacation year round. It is exactly what we want, we don't have to fight traffic and that 40K, well we can find other ways to spend that. We sold most of our DVC contracts and have pretty much moved on.
I would spend 3-4 weeks at WDW to test drive the concept. We were the WDW poster children for decades so our decision surprised even us. Good luck!