I am relatively new to timesharing, so I can only share my limited experience. I have stayed at timeshares a total of 59 days, and my average cost has been $99.90 (this includes all exchange fees and maintenance fees, but not the initial purchase price of my timeshares, which were low.) For that $99.90, I have stayed in mostly 2 bedroom accomodations, with one being a 3 bedroom and two units being a 1 bedroom. All were gold crown or premier resorts. While I understand the value of saving money with priceline and the like, I appreciate, even when staying at hotels, knowing exactly what quality I am getting and where I am going before hand. I am not comfortable with finding out where I am going after I pay.
Contrast that $99.90/night with a trip I am taking tomorrow to the "Springhill Suites" about 3 hours away for a graduation. I will be paying with tax $122.08 for basically a studio hotel room with a little sitting area separated by a half wall and a mini fridge. A lot tinier and much lesser in quality for more money. This is really pissing me off actually! I was telling my husband last week that this is going to suck because we will be stuck in the same room with our teenage daughter and no kitchen, no separate bedroom or bathroom, or real living room. To top it off, I am paying more for the "privilege"!
Yes, there is the food cost savings. We went to DC for the inauguration in 2008 and there were 8 of us in a 2 bedroom - 4 of which were teenagers - we went out to eat dinner once at a modest place, and it was over $250 with tip. We ate in the rest of the week, I saved at least a grand on that - if not more! I mean, every afternoon, we would stop at the Dunkin' Donuts across the street when heading in to the timeshare for the night and these kids would eat the whole dozen donuts before I came back out of the bedroom, after changing into more comfortable clothes (less than 5 minutes' time). They were like locusts!!! I spent probably $350+ at the grocery store that week and felt lucky to get away with just that!
Plus, there was a lot of family togetherness in cooking meals and hanging out together that created a lot more memories among the cousins (the teens) , then they would have if we had just shuttled them from restaurant to restaurant 3 times a day for a week. They could get up in the morning and goof off togehter while eating cereal or making bacon and eggs, watching TV or surfing the internet together watching youtube videos and laughing hysterically, etc, while the parents were still in bed. Since we live in IL and they live in FL, they rarely see each other. They all still talk about that trip as being the best vacation of their (short) lives, and want to vacation with us again, I doubt that those memories would have been created in "2 adjoining studio hotel rooms".
Also, the washer and dryer totally came in handy. It was not in the unit, but down the hall (usually they are in the unit though). Knowing you will have that does help you pack less. I usually bring only a carry on for the week.
To me there is also a comfort factor of NOT having someone come into my room every day to "pick up" after me. I always feel like I need to clean at least a little for the maid before she comes, I don't have that feeling in a timeshare.
Finally, it does "force" you to use it or lose it with the timeshare vacations. You view it as a missed oppurtunity, since you have the sunk cost regardless. So, you always find a way to make a vacation work somewhere, sometime during the year. Otherwise, it's too easy to say, I'm too busy, maybe next year. Once it becomes, "I will waste this $XXX (or worse $X,XXX) maintenance fee if I don't use this timeshare", believe me, you find a way to use it.