But reading through your stories inspired me
I had this conversation with one of my kids recently. They don't remember what it was like when we were starting out. Money was
tight then--to the point where we bounced a handful of checks in the first year or two! But that was when we had one income, a mortgage that was just a bit outside my (admittedly conservative) comfort zone, and a healthy balance left on the loans my parnter took out to get their MD. Our first vacation once we had started our family was a three night stay in Toledo
. That's Toledo, Ohio, not Toledo, Spain. We stayed in a budget version of a Residence Inn, went to the zoo and the science museum, and hung out. To say it was modest would be an understatement.
To this day, that was one of the most memorable vacations I've ever taken.
As time progressed, the second income ramped up, the debt was gradually paid off, and the mortgage payment mostly stayed the same! So, our discretionary budget grew as well.
Our Disney trips followed a similar pattern. The early days were on the cheap, and we did things like choose airports a few hours' drive away to save on airfare, renting offsite VRBO or timeshare units and once even my uncle's vacation home in Clermont at the "family discount". We would splurge on one or
maybe two sit-down meals over the course of a week. And as we had more discretionary income to work with, we started using some of it to upgrade our vacations, at Disney and elsewhere. I also had an angle that got me into
DVC villas for a very attractive cost; in exchange I had much less flexibility in resort, unit size, etc.
The upshot of all of this is: we didn't need to have All The Disney Things from the beginning. We started out small, because that's what we could afford.