@FL Guy If any of them want it, add them before you pass. It seems to be a real headache for the heirs who want the Wyndham timeshare. Multiple times submitting the death certificate only to have them "lose" the paperwork again. I've seen people posting that 6 months to a year later Wyndham still hadn't done anything. Maintenance fees still have to be paid, they can't use the account, and it ran into the next use year so all the points from the previous year were lost.
Several things to be considered for anyone considering this. Is there a VIP level with grandfathered unlimited housekeeping credits? If so everyone definitely wants this to be as seamless as possible. Is everything developer, resale, or a mix of both? Are there multiple contracts in the account?
Yes, you're Gold with your PIC and have several deeds/contracts. First you'll have to add them to the deeds. Since there isn't a deed involved with CWA contracts, that's an in-house thing Wyndham handles. Afaik after all that's done you'll submit the Wyndham form with the $399 payment for each deed and contract.
I've seen people post that the Legacy department will handle this and there might or might not be fees. Same thing with the Title department. All you can do is ask. You might want to keep calling back to see if you'll get a more favorable answer rather than accepting their first answer if all you're getting is no, no, and no.
Technically all you need to do for now is add them to one deed or contract in the account to make them owners. However that just postpones the eventual headache. However that's still a good way for them to try it on for size.
PIC Plus weeks aren't transferable. So you can't change that. It's always handy to have extra names on the account so my solution would be to not take you off the account when you pass. Many owners do that when a parent passes to have the extra name(s). This is a don't ask, don't tell situation. They just have to make sure to keep paying the maintenance fees for the resort you PIC'd. The points count towards your VIP level even if they don't deposit the week.
I'm guessing from your post that your PIC Plus week might be a 2 bedroom that gets you 154k points? At some point you and/or they could find two 3 or 4 bedroom weeks that would give you/them a total of 508k PIC Plus points. You'd unenroll your current PIC Plus week to enroll the higher point weeks and have to make a 98k point purchase. There's a maximum of two PIC Plus weeks allowed. You'd make them the primary on those PIC Plus weeks and the primary on the new purchase too. I'd estimate this would cost in the neighborhood of maybe no more than $20k if you go though Telesales and don't mind having more CWA points. Youll get bonus points and the discounts and rebates typically start at 100k-105k depending on the current promotions. Sometimes they're enough better for 120-130k points making that a much better deal for just a couple k more.
The Massanutten resorts and the Williamsburg Vacation Village resorts have 4 bedroom units and you should be able to pick them up for the closing costs and fees. I think one of the VV Williamsburg resorts has 3 bedroom units. The owner might even be willing to pay the closing costs and fees or split them with you.
That 508k PIC Plus points plus the additional 100-130k points youd be buying should be enough to make you and them Platinum. Maybe even Founder's? I'd guess the bonus points would for sure be enough make you and them temporary Founders for 2 years.
Lots to think about and discuss.