We are about to embark on a gold plan vacation. The best thing about the plan is not being a cheapskate once you get there. I was digging through stuff from our honeymoon and it looks like we shared plates and ate a lot of counter service. Not this trip! Also, you get to do the tours, which we love, and unlimited recreation. I would have never splurged for parasailing while at WDW before. You can also really get your moneys' worth with golf.
On the downside, a lot of planning is required to make sure you get the most out of the plan and don't lose money. For some, planning is the most fun part and for others it's a drag - kind of a personal preference thing. For our trip, we have a pretty detailed itinerary with 22 PSs, 5 tours, Cirque, parasailing reservations, parade viewing area reservations, etc. I thought it was kinda fun to work all that out, but I could see some people not liking that much structure.