I bought into Boardwalk in 1996 when it first opened - the points back then were something like $63 per point - so it was a massive bargain compared to today. I bought all of my points at once - 440 - enough to cover staying for 10 days peak season in a mix of 1-2 bedrooms...knowing that my actual stays would be at different point levels throughout the year, and mixing in occasional studios, so those points would easily stretch to cover 15-20 days a year, enough for 4 to 5 trips of 4 days each...which has remained true through to today.
I was 27 when I first bought in - I lived in S Florida, and had my parents and my brother both living nearby in the same town, so we often had annual family trips, and I'd take other trips solo or with friends during the year.
I've been with Raymond James, a financial services company, for 31 years now - I had been with them 2 years when I purchased DVC. I tend to only spend money on things I really like - I don't have too many expensive vices or habits, and I'm not big on designer clothes, new phones and electronics every year, and other costly little add-ups that many of my friends and relatives are into...when I splurge, it's usually on watches, cars, and travel - three things I like the most. Even then, I don't buy Ferraris and Rolexes - I might buy a nice sporty car every 3-4 years under $55K and a 'commuter' every 4-5 years in the $30-35K range...as long as it's something I like the look of, comes in a cool color, or is something you don't see every day on the road. I can be just as happy buying a $150 watch as a $10,000 watch, if it's a cool design or interesting complexity. Because I live just a few hours' drive to Disney, having DVC and an annual pass means when I go, I don't really have any real trip costs - the gas to get there, and whatever food and drink I buy while there...so I can enjoy and splurge each trip with good restaurants or bar tabs knowing DIsney is overpriced - most of the year, I cook my own meals.
I've gone to Disney with some friends who comment on how expensive it is and how can I always go to these expensive restaurants, deal with the pricy drinks, the valet fees, and so on - then I break down how much they spend on daily take-out or delivery lunches, restaurant meals every night, 100 pairs of shoes and some designer bags every month or two, 10 different streaming service subscriptions, etc...all things I don't have to deal with - add up 3 months worth of those expenses, and it would more than cover my pricey splurges at Disney every 3 months or so. We each buy what makes us happy and is within our means - they just happen to be different things!