Currently, we own 11 timeshares, and except for one developer purchase, I acquired all of the rest for cheap or free on the resale market - mostly from the TUG Bargain Deals Forum, eBay, and personal contacts. At this point, if I acquire a new timeshare, I try to give one away. Most of our timeshares were acquired for our own use, and some of them can be rented for a profit. We acquired two SDO weeks, because they are strong II traders for Westin Resorts:
4 Westin/Sheraton
5 Wyndham (weeks not points)
1 Hyatt
1 Independent
We are self-employed and work from home, so we can work on vacation from anywhere with decent internet. We didn't travel in 2020, 2021, or for most of 2022, so I have a lot of exchange company deposits to use up. Right now I have about 10 exchanges lined up for the next 2 years, and we used 3 exchanges recently.
Owning a lot of timeshares successfully boils down to 3 things:
1) You must have some discretionary income, because maintenance fees will go up, and things can go wrong sometimes. (I own 4 OF weeks at a resort that's going belly up: Wyndham Kauai Beach Villas.)
2) You must be an advance planner - 12 mos. or more out.
3) You must be willing to learn the ever changing detailed rules of ownership, and apply them consistently. I know intelligent, professional people who procrastinate about paying thier maintenance fees on time, and making their reservations on time, and miss important deadlines.