Many years ago I bought a timeshare, off the internet, sight unseen and HAVE NEVER BEEN THERE, for only $300. It is outside the Orlando area---Lake Hartwell, South Carolina. yes--three hundred dollars total. It is life-time deeded and I can "will" it to my son. I bought what is called a "red week"--which is the highest 'value" and in a regular resort--not Gold Crown or anything spectacular. I pay a yearly $311 maintenance fee, $89 to belong to RCI and then $149 to exchange into the Orlando area. So for roughly $550 I have been able to get 2 - 3 bedroom condos, Gold Crown status in the Orlando area for our vacations. That being said--we normally do off season trips. At peak times I find I run the risk of getting just "standard" units--which are still usually nicer than just a hotel room. (But I just use that as an excuse to stay onsite). I have been unable to exchange to the beach in July but have never had a problem with getting something in the Orlando area at anytime.
While I think I would love to own in the Orlando area, the purchase price is always WAAAAAYYYY higher than the $300 I paid, the maintenance fees are a lot higher, I don't want to be tied into the same week at the same place each year, and for what I paid up front I feel I get good value for money exchanging what I own--even with the fee. The resale market of timeshares is lousy so unless it was something I was POSITIVE would work every year for me I'd be leary of making that big of a purchase. You also need to think of the way you will vacation in the future--for instance, once you have kids will you want to stay onsite to give them that experience, will you vacation with grandparents in tow so need the space a condo has, etc etc.
I also think the economy has an impact on how I travel/how much of a deal I think my timeshare is. When the economy is good, people are traveling, hotel room deals are harder to find. When the economy is not so good, you can find hotel deals that work out cheaper/almost as cheap as owning a timehsare. For instance, I have a 3 bedroom unit at Hilton grand Vacation Club reserved in January. Disney runs rates of $49 per night in the Values for AP holders. My DGS is DYING to go to Pop--for 7 nights at Pop it would be roughly $385. Less $$$ than my timeshare, not as much room as a 3 bedroom, but onsite and would make my DGS happy. Plus, as others have mentioned--through skyauction, and other means you can find deals on condos. If you are a Government employee--of any kind of Government not just Federal--- RCI has the
www.getravelop.com website that allows you to rent their excess inventory for $264 per week.
I would not pay a large of sum of money to own a timeshare, but for what I paid I feel I got a good deal and am usually happy with it. I did try to sell it this past year but the Ebay deal feel through so I have decided to keep it.
It's probably not what you want to hear, but no good news from them. I have no interest in slotting my family into one vacation in one location year after year. Even with WDW, we like to rotate with other trips. My advice is to pass and set that money aside in a liquid interest bearing account to use for your vacations. 
he had to explain it to her 3 x that she could ONLY stay at one in the books)
). They also offered an every other year program (for less than the every year plan) and you used the RCI system on the off years.
