An outsider looking in, I can't imagine how timeshares EVER make sense. The whole thing wreaks of a scheme a-la MLM or some other nonsense. In this era of AirBnB or VRBO, I don't know how one can make a case for a timeshares.
Folks, just a couple of years ago I flew to Curacao with a girlfriend, rented a bungalow overlooking the water (could walk to the caribbean down the steps) and rented a car for a week, all for about $2000.
As a non-risk taking midwestern cracker with kids and a spouse that has to book vacation time at least 6+ months out, my vacationing options are somewhat limited to more traditional vacation spots.
I have to work around school schedules, really don't want to pay a lot for airfare, and just really don't want to rent a bungalo and spend a week in it with 2 young kids

. Just my wife and I, sure. But kids really throw a wrench in what I'm comfortable renting and where I want to go. And how I get there.
I've been pretty clear that I don't think timeshares are a great value. And not all time shares are created equal. I've spent a lot of time over at tugbbs and Hilton is praised as probably one of the best out there. But it comes at a premium. The Wyndham ones are decent, but Hilton's properties, their customer service, and options are a couple cuts above most.
If you buy direct from Hilton you are going to be screwed. Hard. The share I bought was probably $35,000 or more for the sucker ahead of me. Some of the Hawaii ones are pushing $50,000 in the primary market. The New York one is upwards of $80,000.
At $7,000 it's still not chump change. But it's paid for and out of the way. So now for about $1200 a year I've got 1-2 weeks worth of travel at a place that has 2-3 bedrooms, a full kitchen and usually very family friendly amenities and in places that have a lot of things for typically family stuff to do. The place I'm deeded at in Myrtle Beach has a lazy river and a mini-golf course on property and is right off the board walk. My week in June there would cost me over $3100 + taxes to rent if I booked in cash.
Same thing with Hawaii trips. A 2 bedroom place there is going to run you $250-$350 a night + taxes easily. A week could be pushing $3,000 or more. 9000 points (pull/push from year to year) and I've got a week there.
With Hilton you can book up to 9 months out for resorts. You can book your home week at your resort up to a year out. I've got a late May date for my home week at Myrtle which doesn't work for kids, but that's fine. 9 months still lets me get in and book a week in the 3BR condos without issue. With as far out as we need to plan our vacations anyway, it works very well for us as a family.
In the event we can sneak out for a weekend getaway to Vegas, I can pay cash rates for a place in Vegas and get booked on the Strip for $70-$90 a night. Or point wise that's 700 points for three nights.
I'm cheap by nature so I hate seeing the daily rates on some things. $300 a night? EEEEK. But now that I've "bought in" I'll accept $1200 a year and not worry about seeing that sticker shock when I place a reservation at a place like Myrtle or Hilton Head (coming next year). It's already paid for. Leftover points for the year can be rolled into the next. Or you can pull from the next year into the current and grandslam on a big trip in the current year.
It's not for everyone. And it's definitely not a value especially when bought directly from Hilton. But if you hunt for deals and know how to work it for the most point value it's not as horrible as the time share horror stories make it out to be.
One thing different about Hilton is that they have a "First Right of Refusal" on most of their properties. By that it means that if you own their property and want to sell it, Hilton has a chance to buy it back first. How this works is, say you bought that Myrtle Property direct from Hilton for $35,000. Decided you hated it for whatever reason and wanted to dump it. You go to a reseller and get it listed. You just want it gone so you list it for $3,000. A buyer comes in and says "I'll take it!". It first has to go to Hilton to see if they want to buy it. At $3000 and 7000 points Hilton is going to buy that back from you. There's no hard and fast rule on what they will buy back. They tend to be more active at some times of the year and won't exercise it on all properties. But usually if you are looking in the 7000 point, platinum properties expect to pay $1 a point or it's going to get bought by Hilton first.
They won't usually do that on every other year plans, so you see those going for cheap. And the 3400 point deals really don't offer a ton of value to buyers (worst thing you can really buy) so they won't buy those back either.
So what that does for the resale market is gives you a bit of a floor value of what you can get back should you resale your resale after a while. If it's a desirable property there's a good chance you can sell it without too much of a beating since Hilton keeps some check on the property values.
For anyone that cares, here's where I bought from:
http://www.sellingtimeshares.net/
They are one of the biggest Hilton second hand market sellers out there. The owner of that company is very invested in the Hilton system and knows it and the buyback activity very well.