We are in a similar position as the OP. I'm 37, wife is 34, and we have three boys, ages 7, 5, and 2. I've posted a lot on these boards about how we arrived at buying DVC late last year. The lodging is either cheaper if you plan on staying in a deluxe for cash or renting points, or you can stay in a deluxe for the cost of a moderate or value resort. Long story short, we booked a week at AoA after visiting in April 2022 as a family for the first time. I remember thinking we would never be able to afford a trip that nice (my parents have DVC and they treated us at OKW.) We invited my parents for the AoA and they told us we might want to save the money and buy DVC resale instead. We found a contract at the Poly we liked and so we bought it. We didn't need to finance it, and had I needed to, I would not have bought it. Yes, buying DVC saves us money on the stay versus the rack rates or renting points, but it does cost us a lot on the actual vacation (airfare, tickets, food, etc.) Our trip in August will run us about $8,000+ before accounting for maintenance fees. And no, we have never spent this much on a vacation, let alone every single year (our finances have seen a nice increase this past year or two and we already save a good percentage for retirement and our boys' college.) It also means we are forced to vacation. While that may seem like a negative (and it might be one day,) it is a positive for my wife and boys, because I'm good at booking a vacation, but I'm terrible at actually following through and going on said vacation. DVC is forcing me to take a vacation and my family cannot be more excited.