For me, I own a diamond Hyatt Legacy week (fka Hyatt Residence Club, nka Hyatt Vacation Club) worth 2,200 points and I am in the process of purchasing another. I use them almost exclusively to stay in 3 resorts. Hyatt High Sierra around early Sept. just after the summer season (1400 points), 4 nights in Carmel (800 points), and a week in the Hyatt Kaanapali which is just awesome (2200 points). I pay about $1650 per year for each 2200 diamond week. Each of these reservations costs about $40 on the internal Hyatt owner's dashboard/site. I like staying in these particular resorts every year (have only done Kaanapali once, which was last month, which is why we are buying the additional week for the points to go back), and I love the value. When we have more time, we will supplement these vacays with a return to European travel and maybe some cruising, none of which will be related to timeshare vacationing. But to the point of the OP thread topic, I think buying a timeshare is a smart thing to do, if it suits your vacation and lifestyle, you understand the costs, and you know how to use what you are buying.