We have been owners for almost six years now.
What is so hard to answer about this question, or at least I believe is that we all change, our families change, we get older, the product evolves, a pandemic hits, etc.
I can't believe my daughter's first trip to Disney was when she was still free and how many times we have been back as she enters middle school. I can't trade those memories of her in an Elsa dress or making sure we see Goofy....every day.
DVC was a huge part of making that happen. We paid cash for BLT our first trip. Sadly, we could have purchased a smallish contract for that same price.
We have stayed in HHI, Grand Californian and our most favorite trip was to Aulani. DVC made that possible.
Even if I take the discounted rack rate for all our trips, we have already paid for it in just about 5 years. I know that takes longer now with rising prices (we averaged about $125 a point). You will hear many say they wish they bought earlier or more points earlier - because prices rise and if you are still coming to Disney with any frequency, the more value you get from DVC.
As as you have seen OPs, we all go "not at these prices" since we paid far less. I keep looking at contracts kicking myself I didn't buy when it was $50-75 a point cheaper and we could have already been using them! I bet even 5 years from now the same discussion and the same grousing about pricing will occur.
Our vacation plans certainly have changed as we have started to visit more places than Disney. I see us using more points for larger spaces as our daughter gets older and wants her own space or brings a friend. DVC makes that possible for us. We can scale back our points since we have three contracts later in life or as life changes. Hopefully, values will still remain but we have gotten our monies and memories worth. If we sell for more than we purchased it is a windfall and unexpected. Am I thrilled with all the changes, of course not but that has not impacted the value and memories we have received.
Plus...life is short and as we have seen last year, nothing is guranteed.