My parents bought several timeshares during their retirement years (Branson, Wapato Point in WA, Cabo, and Puerto Vallarta). Mother bought another in SF after Dad passed. On the up side, there were several family vacations at Wapato and a couple in Cabo over the years. The Branson and PV timeshares were not used, but they traded points for upgrades in Cabo. Mom spent a lot of time and got pretty good at figuring out trades, points, etc., but she paid extra for RCI and Wyndham programs that allowed her to play with week/points. She traveled until the last 18 months of her life and never did use the SF unit. I was the executor for her "very small estate". The timeshares ended up being the hardest part of settling her estate. I was able to turn back the Wapato unit for a small title transfer fee. After much work the same was true for the Mexico timeshares (both Pueblo Bonito). However, I had to go through probate process in both CA and MO to turn back those units paying attorney and title transfer costs. It was a very stressful time for me as no one in family was interested in taking on any of the timeshare units. Also could not close out probate for estate without unloading the timeshares (unless estate wanted to continue to pay maintenance fees).
I tried donating to charity - none were interested. Looked at possibly selling, but there are already a ton for sale on secondary market. I offered them free to friends - none interested. The estate ended up paying maintenance fees for the 18 months it took to unload the MO and CA units.
Upon reflection, my parents could have traveled quite nicely for the amount they ended up paying for the purchase and maintenance fees. I'm totally turned off of timeshares after having to go through the hell of getting rid of them. Even if you buy the timeshare on the secondary market - how will you get rid of it when you are done?