Very interesting stories from all of you.
Mine is similar in some parts and different in others. I've been a long time Disney Parks fan, living on the west coast in the Vancouver, Canada area. I remember hearing about DVC when it first started up (I was in my late teens at the time) and thought about how great that would be but couldn't imaging being a grown up with enough money to do anything like that. Fast forward several years and in 2005 at the age of 30 I was married with a 6 month old son on a trip with my DW and parents to WDW. We decided to take the DVC tour just to see what it was about. We toured SSR at that time but weren't ready to commit, liked but didn't love SSR, and I had wanted to learn more about resale so after getting home the research started, with a lot of that here on the DISBoards back in 2005! See my "Joined" date?
Within about a month I had purchased a resale BWV "loaded" contract for 150 points based on a plan to go every second year and stay in a 1BR. I rented all the banked and current year points to offset some of the purchase costs and then saved up 3 years worth of points to do a big 2 week trip with 1 week of that in a 2BR with my sister and parents as a "thank you" for all the times they brought me as a kid. And by then we had a daughter as well. I loved our choice of the BWV and my wife and I decided we would like to be able to stay in a Boardwalk View anytime we went so we added on another 50 points.
In 2010 we stayed at VGC just days after it opened and we really debated adding on but didn't at the time. However, a year later we made another trip to
Disneyland after some personal struggles and decided that while we were OK staying off property in Anaheim we really wanted to stay in the Disney bubble so we jumped on a tour and added on 165 points (115 and 50 point contracts so we could sell 50 later if we wanted).
So getting back to the topic of this thread, being an engineer, this was all based on calculated point usage going to WDW and DL on alternating years for the next 15+ years while we had kids and then holding on for a while until they had children and we could start the cycle again as grandparents for a few years until BWV expires when I'm 68. I had the rough idea in my head of stretching points in studios for extended stays in the winters of several weeks when retirement came around and maybe purchasing some near end of life contracts for hopefully inexpensive amounts to hold on into my early 70's and turn those studios into 1BR's.
In the years since, on top of several DL and WDW trips including multiple RunDisney events we've stayed at VB, AUL, and rented out points to take a few Disney cruises, and shared trips with extended family several times. All great uses of points and my wife and I agreed that the DVC purchases were a really good choice for our family during all the toddler, tween, and early teen years. "Plan A" for the first 14-15 years worked really well.
HOWEVER (record scratch sound effect?) in late 2019, my wife and I separated and are finishing up divorce paperwork now. Amicable but there were many underlying problems. My DD15 still loves Disney and the parks, but my DS16 is in a phase where he feels he can't enjoy "kid stuff" anymore. Through the divorce process, I decided to hang onto the DVC points and paid out my portion for them. I was always the bigger "Disney person" and holding on to them was partially an emotional/comfort decision but I also know they are an asset that could be sold later if needed because of how the contracts were set up in smaller increments and I likely wouldn't repurchase new points now for today's price compared with what we paid for them in 2005 and 2011. And on top of that during COVID, the Canada/US border has been closed to leisure travel so between my separation and COVID, I've only had a weekend in 2019 with my daughter at WDW tacked on to a work trip to Orlando and before that my last major Disney trips were in 2017. I've rented out points the last several years, first to fund an Alaska RCL cruise in 2018 for my family and another Spring 2019 trip elsewhere, and after that just to try and use points that would expire otherwise while I couldn't/can't travel across the US border.
So today I'm a 46 year old single Dad of two teenagers, one of which isn't really interested in Disney anymore (or at least for now, until he grows up a bit and has his own kids) and I've got 365 points between BWV and VGC and no clear plan for how I will be using them in the future. I'm sharing some with my sister as a post wedding stay at VGC for her in the Spring and I hope to get another 4 day weekend with my daughter in November before another Orlando work trip, then hang on after for several days at VB on my own as some quiet mental decompression time after the last couple years of personal stress between death of both a parent and grandparent, separating, COVID, plus working in a company under some serious COVID-driven financial distress.
So Plan A phase 1 (young kid time) worked well. Plan A phase 2 (post-young kid time) not so much. Time to come up with Plan B...
That's my DVC story (and more) so far. I'm still happy to have the points as it keeps me thinking about getting out the door on vacation, well at least when I'm able to travel again from Canada. Selling off 50 points of each of the BWV and VGC contracts may be in the cards as I don't see myself using as many points in my current situation for some time and retirement is still 15-20 years away. But it would be nice to have them later when my kids start having their own children and I do like to share them with extended family too. I'll wait a bit and see. If I end up continuing to rent out out the majority of them even after COVID that's a pretty clear sign that it's time to let them go. We'll see in the next 1-2 years where life goes next.