I would say deciding on a whim (because it wasn't much more/night) to choose Club Level the first time our whole family went 6 years ago. It was perfect for us, especially when we were there with my older parents. Have been back twice since and done club again both times.
That was my first thought when i saw the question. Our first family trip back to WDW was when my DGD was 4, and we were not sure how she would react to the parks, the characters, or just the trip in general. We also were planing when WDR's were 90 days out and CRT was still one dining credit, and there were all kinds of horror stories about securing this one (a must for us that trip) WE decided to bite the bullet and book CL for both of our rooms, and never looked back! My poor DH, who was suffering sticker shock that started when we told him the cost of AKL CL Savannah view, and continued for the first few days of the trip until we reminded him the cost of NYC meals and lodging, told me that this was the best money we ever spent.
WE do not book CL every trip, but we do decide what kind of vacation we are planning and what our preplanning needs will be , as well as how we want to tour. CL is sometimes worth the cost even before we get to the resort and the stay is a bonus! LOL!
Making WDW a family tradition when our children were small. We tried to go once a year and even now that they are almost grown, it feels like HOME to them even if we don't go as often.
Yes! After that first trip with our DGD, my DH promised me that his goal was to ensure our precious Kady was able to visit WDW at least once a year, if not twice, until SHE was ready to slow down. And he made good on that promise! My DD and DSIL love WDW, so they were on board, and I sure never refuse a trip, so it was a great plan. WE are now introducing our DGD's of our hearts to WDW in August, and I can see my DH making sure these two Princesses get to go every year if they want and their Mom agrees. WE have named our trip 'Ohana, and the girls know that 'Ohana means Family, and Family means no one gets let behind or forgotten. They have never questioned that even though we are not bonded by blood we are family, but this is the first time their Mom agreed to come even though her funds could not cover the cost, because we are , you know.....Family!