I purchased a week in Orlando four years ago and am in the process of buying an additional unit in the system right now. There's been a lot of good advice posted but most importantly that your happiness with the purchase will depend on your personal situation.

For my family, it was not one of the wisest financial decisions we've made, but it's been one of the best. Prior to owning the timeshare, we had not taken a family vacation of more than three days in eight years. Pre-paying for one and having disincentives for not planning one in advance has been the motivation we needed all along. Now we vacation with grandparents. We've booked a combination of timeshare nights and nearby hotel nights with HHonors points. We've converted into the hotel system for nice, vacations closer to home. In short, it's been exactly what they promised. The flexibility of the system has been a great asset as we have never used exactly what we own (size & season).

Now for the downsides. I purchased (the first time) from HGVC and I estimate that I'll be whole, financially speaking, in 8 more years. This time I'm buying resale at less than half what I paid. I figure it will take about five years to break even (purchase price divided by the difference between the weekly rental cost and the maintenance, taxes & membership fees). If you purchase a Hilton-owned property resale, they can (and do) exercise a first right of refusal if the price is too attractive. This allows them to keep the values up and to "upgrade" current owners for the difference of full original purchase price. If you purchase a HGVC-managed resort, you might find a lower price yet still be able to exchange in the HGVC/HiltonHHonors system. Checkout Redweek.com and eBay for resale listings.

The greatest disappointment for me thus far was when Hilton changed the redemption schedule for hotel rooms from 150K for 6 Nights @ a Premium hotel, 100K for others, to 175K for a Category 6 and 150K for all others, effectively devaluing my timeshare. They also raised the Cat. 6 from 35K/N to 40K/N. The truth of the matter is that they can do this again and the HGVC/HHonors point conversion of 1:23 remains unchanged. For that reason, you should carefully consider your purchase if you don't intend to stay in one of the timeshare properties. Ownership guarantees you Silver VIP membership and the ability to book GLON certificates, but limited hotel availability for Silver and Gold members is a problem. If there's a chance you won't remain Diamond (and even if you do), you're probably better off paying cash to book what you want, when you want, if you prefer staying in Hilton hotels.