For me, it's all about options. If you rent a hotel room, you get what you get, and I've seen enough dumpster views from spendy hotel rooms to last a lifetime. I want to be able to count on better accommodations.
I owned an oceanfront resort on Kauai for a long time, and my vacations there were in the same prime unit every time. I knew before I arrived exactly what I'd be getting for my money. I never exchanged that ownership. Selling it was a hard choice, but I did it only after buying a week in an affiliated resort group. That gives me options of exchanging back in to the same resort (but maybe not the same unit), but also being able to internally exchange to other places in their system, for lower maintenance fees. My next vacation will be in a great oceanfront location on Maui, which I got for about a third of the maintenance fee cost of owning there, and for a fraction of what hotel rooms rent for in the area.
But then, after all these years, I have also just bought into WorldMark so I'd gain the additional flexibility of short stays, last minute stuff, and all the perks, in addition of being able to have long-term planned trips to places I'd like to go, where an exchange may not be available.
The other thing I like is maintaining my membership in RCI, (without exchanging), which gives me access to Last Minute and Extra Vacations, so cash-based options are increased. I have a coworker who is currently in Las Vegas at the huge SEMA auto trade show, a major event he likes attending every year. I was able to get him a great two-bedroom unit not far from the venue. He is sharing the cost with a close car buddy friend, and they're each paying about $35 a night to stay there. Hotel rooms there have been booked out for a long time. We've done this sort of thing several times.
It's all about the options. And choices.
Dave