I assume you already have your family trust set up and that you know the pros/cons of having ALL your assets in the family trust. Most of our timeshares are in our family trust. The ones that aren't get a 'shame on you' from our attorney and a 'I'll get to it at some point' response from me. It's best to put your timeshares in your trust if it's your intent to have them passed them on in a stress free manner when the inevitable occurs. I would put them in the trust at the time of purchase as it's a heck of a lot easier (and cheaper) to do it when making the purchase than it is to chase down an attorney, sometimes in another state, when you finally decide that the timeshares should be in the trust along with everything else you plan on passing along. We've not have problems putting non-Wyndham timeshares in our trust.
The process with a Wyndham Developer purchase is a multi-step process, when I did it last, and there was an extra charge involved (less than $200, if I recall). We have a recent purchase that I currently need to move to the trust, but, we've decided to have a chat with the Adult Children before we actually make the effort to get it done. We think we know what they want us to do, but, we need to confirm. They do use our points from time to time. If they want the timeshares, we really need to make sure that we've put them in the trust. Our view on the family trust is that it's just another gift, the gift of simplicity with settling an estate. We're very good about having our assets in the trust or having the trust set as the beneficiary/TOD for an asset.
On another issue, do you mind sharing the Timeshares you chose for your PIC's. I contemplating the purchase of a 3BR to replace a 2BR we currently have PIC'd?