I am going through past postings (there sure a lot to wade through), and thought I would add my two cents' worth here (in other words, roughly the financial value of a timeshare) because this (like others) caught my interest. I've been talking to my boys about timeshares, and as of now, they are not interested. They might change their minds in the future, but as of now, they are happy, for example, going to Las Vegas (where one of them happens to live) and staying in a hotel in the middle of all the action. I even told them there are some timeshares on the strip. They tell me, which I find a little hard to believe, that they can stay (and have) in nice hotels comparable to what I get at Grandview on "last call" or "on sale" deals for about the same cost (maybe slightly more). This could be true when you factor in costs like RCI dues and maintenance fees, which I have explained to them. I mentioned Orlando, where they might want to take their families to Disney World and stay in a nice place. Still no interest. I mentioned one of the things I like - getting up and fixing breakfast in your own room instead of going to a restaurant. Still no interest. They are happy to go out or tell me that there are reasonably priced hotel rooms with cooking facilities.
They do not want to inherit timeshares. And even if they were interested, quite frankly I am not sure I would want to put them through the trouble and extra expense of out-of-state ancillary probate proceedings to deal with these through my estate. If they want timeshares in the future, they can by them at a small resale cost (if not for free).
From reading other postings, it looks like there are people who inherited their parents' timeshares and are perfectly happy. (On the other hand, it looks like there are more who are frustrated with what they inherited and are looking for a way out.) This could be because they enjoy timesharing themselves, or it could be because it brings back memories of past times with their parents in their timeshares.
I'm obviously unaware of what the original poster's situation and motivation is. It's possible that some people, knowing they paid a developer big bucks for the timeshare weeks in the first place, are under the likely mistaken impression that they have valuable timeshare assets, when in reality what they have is worth small bucks now (if anything). And they want to make sure these "valuable" assets are handled properly after their deaths. It's possible that some people may have a sentimental or emotional attachment to their timeshares because they love to go to them.
But timeshares are different than family homes. Homes have real value, and they have sentimental or emotional value as well (even though homes are likely to be sold upon death). But timeshares have no significant (if any) value as real estate. If they are not wanted, and unless the children properly and successfully disclaim them as part of their inheritance (a process itself that sounds like it would add some expense to administering an estate), they become a financial burden with the maintenance fees.
So, what to do?
I think I will keep the timeshares as long as I want them and as long as I want to use them. It's possible that I may reach a point where I might be unable to travel. At some point (which I hope is in the far distant future), unless the boys tell me they want them, I will get rid of them. I do not really want the timeshares in my estate if the boys do not want them. If they change their minds and tell me they want them, it might be a good idea to go through the expense at some point of transferring the deeds for whatever they want to whoever wants it.
But what about an earlier untimely demise before I can get rid of the timeshares? I may not reach that "far distant future." I probably will tell the boys what my overall plan is (above), but I think I also will leave a letter about the timeshares with my will and with my timeshare papers. This letter will say something along the lines that I intended to get rid of these timeshares, but obviously I did not get around to doing that. I will tell them that they can accept the timeshares as an inheritance if they wish, but they have my full blessing if they want to disclaim the timeshares (and I will explain how to do that). They need to be educated about this because they will need to discuss it with the attorney handling the estate.
The original poster mentioned the possibility of setting up a trust for the purpose of paying future maintenance fees. I would not do that, just as I would not set up a trust to pay future real estate taxes on my home. Presumably, if the children inherit the timeshares and then want to get rid of them later, the money in the trust would revert to them anyway. (I doubt if the intent was to pay future maintenance fees on behalf of some future buyer!) If they want the timeshares, they can handle the maintenance fees, just as one or more of them would pay future real estate taxes if they decided to live in my home.
If I were inclined to set up a trust so they could enjoy future vacations, I would just set up a trust to be distributed to them over time and they could use the money however they see fit. They might know my intent was for them to use it as "vacation" money, but I would not want to tie them to that. And they might really need the money for something else. There are sometimes good reasons for setting up trust funds in general, though.
The family trust concept sounds interesting. It sounds like this means the timeshares are titled in the name of the trust. If so, that might bypass probate, except trusts cannot legally last forever. Someone still has to pay the maintenance fees. Eventually, with grandchildren added into the mix, there could be a lot of people who have rights through the trust to use the timeshares. And someone will be chasing down all of the grandchildren and great-grandchildren to pay their shares of those maintenance fees (unless as the original poster suggested, funds for this are in the trust). And eventually, at the end of the trust, someone still will have to figure out what to do with the timeshares, unless the timeshare has become obsolete in the meantime. The other thing about trusts is that there has to be a trustee. Surely, unless you have a huge estate in the trust, you wouldn't want to hire a bank as a trustee to keep track of timeshares that are basically not worth anything financially. Wouldn't this mean that one of your descendants would be tasked with keeping track of this and chasing down everyone?
I'd be interested in hearing the pros and cons of putting the timeshares in the name of a trust (probably will find the answer as I continue to wade through this forum). I'd also be interested in hearing whether any developers have refused to accept deeds transferred to a trust.