Not buying in during that first trip ended up being a good thing because obviously you pretty much hit the jackpot in terms of location a few years later!
its a never ending cycle... it feels cool... then you wonder are the cool kids the ones who stay CL? are the cool kids the ones who live at Golden Oak? or belong to club 33?
I just say enjoy what brings you joy... don't worry about being one of the cool kids...
Did not grow up going to the parks. First time I was 19, and walk in straight into the Utilidors as a Cast Member. Magic got me almost immediately. Few years later, I started dating this girl who shared the same Disney vibe I had and we start going annually and this is the first time we researched but the upfront money seemed huge and the maintenance fees were more expensive them the hotels we were booking so it made no sense. Moved out of the USA and spent almost 10 years away from the parks in a time I travelled around the world, got married to that girl and had a kid. When the kid turned 5, we celebrated with her first trip to WDW. Eyes lit up. SOLD. Next week we were on research mode and 2 months later we got a piece of the Poly to call our own.
Going to Aulani next week....Life is good.
I purchased DVC after visiting WDW multiple times annually for years and paying to stay in deluxe resorts. I refused to pay rack rate and got tired of chasing bounceback, AP, Disney Visa, etc discounts. I was already planning 180+ days in advance at the time so booking in the 11-month window was no problem.