Depends on who I'm talking to.
It's a regular topic of lunchtime cafeteria conversation at work. (My coworkers and I share a large table for lunch.) I've developed a reputation for being something of a vacation hound, and I frequently get asked, "So where are you going next?" People tend to be impressed by the variety of vacations I take, and I am often asked how I can afford to do this. Everyone I work with directly knows I own timeshare(s), so I get some envious comments from them, like, "Gee, I wish *I* could go on vacation with you!" and "I never get to go anywhere..."
Others at work who don't know my backstory who hear I'm going on vacation AGAIN, are prone to ask, "Wow, what are you - RICH?" I tell them No, but that I plan my time off a year or more in advance, so I have time to plan ahead, prepay things like airfare and such, so the travel costs become secondary, and it's very affordable for me to go. I remind them that great vacations aren't accidental - they require planning and effort to pull together.
The worst of the lot are those who cringe when they hear the word "timeshare" coming from me. "Oh, you own one of those??? My sister/parents/cousin/whoever owns one, and they hate it. They spend so much on it, and they never get to use it. What a waste of money!" I've tried to educate people to learn to use what they own, and I tell them about TUG, but only a few have ever done anything about it.
One woman asked if I could help her learn what to do with her two timeshares she owns. I spent a lot of time telling her about stuff, how to maximize her ownership, and whatever. She goes away on a vacation, and can't wait to get back and tell me how she and her husband made such a GREAT deal during the presentation they attended. For only $$$$ they were able to trade in their other timeshares for a new one! (You all know how that ends - she later said she didn't know what to do, she'd received a new bill for maintenance fees on the traded-in timeshares, she couldn't afford things, how she wishes she'd never bought in the first place, and so forth.)
The stories are legion. Results are variable. So while I don't generally volunteer that I own timeshares unless asked, I find I have to defend my ownership to those who have a negative attitude about them. It used to bother me, but now I just shake my head, and agree that their situation is a tough one. Then I pack my suitcase and drive to the airport, heading for my next vacation.
Dave