Let me preface with saying I have not stayed onsite since I was 8 in the campground.
BUT--being the frugal person I am, I can't comprehend spending the extra money. In May, we will be staying "offsite" at Wyndham Bonnet Creek, which is right next to the "onsite" Carribean Beach Resort. I am paying $113/night (including taxes) for a 3 bd/2ba condo, full kitchen, washer/dryer with free shuttles to the parks (along with pools, lazy rivers, activity centers, mini golf, and more). The exact same week, I would have to pay for TWO rooms at CBR, at an avg of $190/night per room (not including taxes). So roughly $3000 for the two rooms, compared to the $795 I am paying. Other than EMH, are there amenities at CBR that I am not seeing that are worth $2000?
I am comparing CBR because they are literally right next to each other. I can't imagine that traveling an extra few parking lots is going to take away the "magic" for us. Our rental car is a little over $200. I have no idea what renting DVC points from someone would cost, but a full kitchen is required for DS's food allergies. And there are 5 adults and two children on the trip.
One day, I would love to stay onsite to see what the hype is, but would never pay the prices for the type of room we would need. Even if it was just DH, DD, DS and I, we would still need a kitchen. (A food allergy mom doesn't have the luxury of not cooking on vacation.

Even with Disney's allergy policies.) A trip for DH and I would work in a value, but never taking the entire fam.
In 2009 we rented a house--4bd/3ba with it's own pool/game room. It was 8 miles from Disney World gates and took us 20 minutes total for the drive. It was an awesome trip! And so relaxing! We paid $650 for the week.
It all depends on what kind of vacation you want. I don't understand how the "magic" is gone if you're not onsite though. The magic is seeing DD in awe watching Tink fly from the castle, or DS at 18 mos waving frantically at Goofy in the
MNSSHP parade yelling "Foofy bike!" OUR magic is also having space to spread out, so I don't become angry mom in a tiny, cramped room.
