My own parents think that "all those poor people who own timeshares in this economy can't get rid of them!" We told them years ago that we'd bought, but I guess they forgot. They don't know anything about the DIS. But they don't have any problem with DH and I going to WDW yearly, or me taking frequent trips without him. Mom went once with me, and although she'd love to go back, Dad won't go.
My in-laws all just feel bad for us-DBIL and his wife got pressured into a timeshare in Orlando and are sure that the reason we own because we got pressured, too. So they think they understand. No one knows that we've ever bought more points-no one understands points, and their eyes glaze over when we try to explain, so we don't. They're tolerant of my solo trips, when DH tells them, "Dorothy's going to WDW alone again" and are more puzzled about him being so supportive of his wife vacationing alone than anything. DMIL went to WDW once with us, and although she liked it, I don't think she loved it (althugh she did enjoy playing golf there).
No one around where we live owns, and not many people have been to WDW, so we don't tell many people about our frequent trips.