Hi Shawn,
This is really a personal question that you need to answer for your family. For my family, it has been a great way to enjoy vacations at the Walt Disney World Resort. For our family, we were able to purchase the membership and stay within our budget. I can give you some tips about how we came to the decision and maybe they can help you:)
First, we loved the idea that we would have points to use versus a set week to vacation. While Disney is the trendsetter on this and other "timeshares" offer this option now it was not an option 11 years ago.
Second, we liked the idea that Disney was going to be around for the life of our membership. We thought this was worth the difference in price between Disney Vacation Club membership and a less expensive timeshare. We also new the quality of the product as well as the quality of the products we could exchange with would be top notch.
Third, we liked that we would know what our "hotel" bill was each year. With our maintenance fees, this becomes our hotel bill. We know our bill is less than if we purchased the same room off the rack. Plus we can increase our days simply by smart planning.
Four, we loved being able to use our points towards other Disney products such as the Disney Cruise Line. Our cruises would not be possible without the membership.
Finally, we did not look at this as an investment monetarily but an investment in our family. Disney is such a magical place we really want to be able to go and just enjoy quality family time. Disney Vacation Club allows us to do this.
I recommend you reach out to a Vacation Advisor and take a tour when you are Disney again. Disney will not even let you buy then even if you want too-you have to wait to purchase. You can call Disney Vacation Club at 877-382-7862 and ask any additional questions.
Wishing you a magical day!
Beth