We knew about timeshares from the time I was a kid. My parents went on vacation to Aruba and were sorely tempted to buy the timeshare they were pitched. In the end, they decided it was unaffordable. So that's pretty much how I saw timeshares- unaffordable and a good way to get ripped off.
During college, vet school and my residency, I was so poor that travel wasn't really a thing for me. Then I was early career with student loans to pay off, and then I took a faculty position and really had no money. Finally I left academia 14 years ago to come out to LA for a job that paid 4x my academic salary. Finally I could think about travel.
My cousin meanwhile had taken a job with DVC and my opinion of timeshares started to change. I found TUG and started buying resale timeshares around a decade ago, when I was in my early 40s.
Now we own quite a few and travel a lot. We really like drive-to destinations so I can bring a bike, and the washer-dryer plus kitchen are huge bonuses to us when travelling- we can pack light and eat appropriately for cycling- ie not much in the morning and right away when back from a ride.
We love our timeshares and have had a weird experience with a Homeaway rental which made us realize that you can definitely get screwed with little recourse with Homeaway and the like, so we prefer the professionalism of most timeshares to private condo or house rentals. BUT the thing that is causing us to rethink the timeshares is the dogs. We enjoy spending time with them and prefer to bring them with us on vacations. Sometimes we think about selling all the timeshares, buying a small RV and dividing our travel between the RV, house rentals and rewards hotel stays at pet friendly places.
We shall see what the future holds.
