Leaving heirs with vacations already paid for, except the maintenance fees, doesn't seem that bad to me.

Seriously, our kids are pleased as punch with timeshare, after enjoying dozens of vacations in luxurious condos, all over this country. They won't mind owning the 19 or so weeks we will leave behind. I taught my daughter about using them to her advantage and she will take the reins in scheduling for herself, her brothers and their families. She also knows how to sell a timeshare and where to list it and what she can expect to get, in the event that something happened that would force her into that position.
We love timeshare and exchanging is the icing on the cake. I think you would do well to buy at a great resort and not put more than a few thousand $$ into the initial purchase. Buy something that will trade well in II and enjoy vacations for much less than you are talking about here.
I think people have such a negative impression of timeshare. It has to do with the way it is presented and the bribes it takes to get people at the presentations in the first place. Plus, there are so many people out there who purchased timeshares and never use them, leaving them to sit year after year, paying maintenance fees for nothing. They should try a vacation now and then!
My niece and nephew own a timeshare at Christie Lodge in Vail, a blue week, but a good resort. When they decided to go to Disneyworld last summer, they rented not one, but TWO hotel rooms at Howard Johnson's. It cost them some crazy amount of money for those two rooms for a week. They didn't know how to join RCI or do the searches, whine, whine, whine, so I told them I could have helped. They left their timeshare unit SIT VACANT that spring because they only have one week of vacation and couldn't use it.

What a waste! They could have stayed at Orange Lake in a 3 bedroom. I saw those all summer last year.
Drives me crazy.