28 year owner at Boardwalk - bought all our points on day 1, no add-ons since (we bought enough to cover the trips we intended - two weeks in a 2-bedroom at Boardwalk during 2 higher-priced seasons and 2 cheaper seasons, It actually works out to about 25-30 days a year when choosing 1-bedrooms, occasional studios, staying at lower point resorts, etc.
My trips have changed over the years - but they're no less enjoyable - just for different reasons. Does that mean I haven't been disappointed with some Disney changes? Of course not - I loved the original fast passes (before you reserved them online even), hate Genie. I find lots of little perks and included services have disappeared or are now charged for. Some restaurants have gone a bit downhill. I don't think I ever encountered a mediocre Disney cast member, let alone a bad one, until the past 5 years or so, where now it's a little more common to get someone who's not quite as friendly or magical. Costs have definitely skyrocketed.
Yet, I still enjoy my trips, and just work around the things that changed. I don't bother to drive my car most places - I just use the Disney transportation. I don't use the Genie system at all - I just decide what to ride based on standby times. As I've aged, hitting as many rides as possible in a day is no longer important...so if the line is over 40 minutes, I can just skip it and plan on trying next visit.
Food, drinks, and entertainment are more important to me now than they used to be. They were still important in my 20s, but I still wanted to go on rides with friends and get in as much as possible. Now in my 50s, I enjoy strolling and walking around the grounds and resorts - I spend probably equal amounts of time in parks as I do in and around various resorts these days. I like some changes - more DVC lounges and resorts are nice - I think restaurants are starting to improve again after dropping a bit since the pandemic...more bars are sprouting up which I like. And various expansions to Disney Springs and the parks have been nice to see - with more coming.
I'm not in-town local, but I'm a 2 1/2 hr drive away local - so Disney trips are still easy to plan - just a quick drive, no airport messes and schedules, packing limitations, and transportation from airports to deal with - I toss whatever I want in my car (I can overpack like a maniac, because there's no real penalty for taking too much), take a short drive, and I'm there. While I'm paying for my Disney trips, most of my expenses are 'pre-paid' - ie: DVC is already purchased, dues are annual, and I buy an annual pass...so all I need to think about when I make my Disney trips is gas to get there, and food & entertainment while staying there.
My trips used to be very family centric - I owned points with my parents who also liked to go, and my brother who lives in the same town could bring his family. Now, my brother doesn't really go anymore and his 3 kids all grew and moved away, both my parents passed away last year, so the trips are now either solo or with friends. Most of my friends have become addicted to Disney trips the way I like to take them - relaxed, no rope-drops, late starts each day, good food and bars, etc. The same way my family liked to do it too - so really little has changed other than who I go with.