Absolutely not, we have no regrets, well.....that's not entirely true

. We wish we bought more points earlier on. Original contract is 185 bought in 2000, with a few small add on's over the years, for a total of 285 points. I always need more!
However, we bought when price per point was lower ($65.00 for the original contract), and the highest we paid per point was $96 for our last 25 point contract. We didn't finance. I can't imagine we'd ever regret it, it's one of the best purchases we ever made, but I think we'd feel alittle different about it if it was a monthly payment over a number of years.
As far as the MF's go, I use all my rewards dollars from my Disney Visa card toward my annual MF payment, and then I pay alittle each month on my Disney Visa card - which we pay in full each month (thereby adding to the earning of more rewards dollars each month) and by the time the annual statement comes in, we're all paid up. So we don't really "feel" the monthly maintenance fees that way.
It's an awesome vacation for all of our family, or just some of us, as the case may be trip to trip, and we, again, feel it's one of the best purchases we ever made. Good luck with your decision!