So I just got into timeshares after probably a decade of thinking about it. And for me it is kind of a cumulation of having more money and working with deals / systems to do things I'd never do for cash rates. I actually started with getting into the Hilton Honors program via the Citi cards (now AmEx) where people were like - $95 annual fee (back in 2009 or so), and I was like, sure, but I get a weekend night at a Hilton pretty much anywhere for that. This got me started "forcing myself to travel".
And most of the same things were [blah blah blah] cheaper if you get a Motel 6. How many Hiltons at Expedia could you get a night for $95? And that's been fixed for 15 years now - that weekend night is still $10k in spend the year and $95. But it's gotten better in that now I think it's any night. Guess how much the retail prices are up? And the points build up. I've had people comment - wow, "you stay in nice hotels". I'm like - sure, but why do you stay in crap ones? I've had people question why I stay in X Hilton, but I'm like, it's actually free for me from card points. And you often get the lowest rates direct from Hilton because you're a gold or higher member. The memories of the great provided breakfasts with family (oh yea, you often get a free breakfast, so count that cost appropriately), the places we've stayed, etc etc.
And a lot of that sort of thing directly is analogous to Timeshares. But they're another step up. You put more in up front, but you get 2 bedroom condos for it. I just did my first stay at a Vacation Village I exchanged into, and for about $1600 in MF and exchange fees and resort fee, I got a full week in Williamsburg, with a full kitchen, 2 bathrooms a living room, a nice resort to walk around, hot tub and pool and game room. The last time I just went to a third party hotel in a tourist area (this was Acadia, so IDK about comparable) but it cost me $1,600 for 3 nights and a one bedroom hotel room. It got to where hotel rooms aren't big enough really to be comfortable. Sure, you can get 2 hotel rooms, but now your cost is way more in a lot of cases. And you can't do any cooking yourself in most of them. So many people discount the actual value on vacation of the included breakfasts or being able to cook yourself, or do laundry etc. If you get one free breakfast that is at least $10 per person at McDonalds now adays. And really, who actually wants to do that? You want to go to a local place (even if fast food) and so that's more expensive. You just take home leftovers from one mean and actually get to eat them the next day and you've halved a meal cost, that again, is often $40 a person or more at a vacation restaurant. You cook one or two meals and the price goes down further.
Ok, so now you know why someone like me might have one Timeshare. Now we ask, why more than one? Well, basically it's to travel more. Often times retail the biggest part of the cost wasn't getting somewhere, but it was where to stay. I realized I'd go to family who put me up WAY more often than if I had to get a hotel. But of course those locations are limited, it's imposing on family which can be a thing, and you're usually only able to come with one or two people - most people don't have a spare house for 5 or more visitors. Multiple timeshares expand where you can travel, what exchanges might be available, and often target different pricepoints too, even in the retail market. Of course, I - being new - am all points, so the amount of weeks owned is a little vague.
Oh, and the other thing, my sister and I like to travel together, and our jobs now let us work from where ever we have internet, so working in the day and doing fun stuff at night or on the weekend in different locations, or maximizing the use of vacation days is part of my plan. My mom is also recently retired, so I'm trying to get her to do some travel that she never felt she could do while she worked.