In terms of "savings" with a timeshare. I see it as $2,000 week for a place that goes for $5,000 a week. So you "save" $3,000 a year. However, you have to factor in the purchase price and the time value or money. Let's say its 10%, in that case you couldn't save anything if you spent over $30,000 on the deed.
Maybe if you model it as a $7,000 a week place, but I truely doubt most people with timeshares would pay that much, unless it was a unicorn week. Even then, it caps at $50,000 and I just don't see it as a guaranteed return.
As Will Rogers said, "I'm more worried about the return of my money, than the return on my money."
With this in mind, the resale value is what worries me the most if I overpay for any asset.
In the end I think people are willing to pay more in MF for availabiltiy and flexability. I mean sure we "own a week at a 2 bedroom" but wouldn't it be nice to get 2 weeks in a studio this trip as the kids/grandkids aren't coming. Then when they are with you splurge on the 2 or 3 bedroom.
Mostly what I see is the optimization trap, which if you solve can be fun puzzle and very rewarding, but its not for novices being the "complicated toy" that timeshares are.