It is challenging to get reliable information anywhere. It was a major concern of my Dad's. Don't laugh, but he would get conflicting advice from sales people (including that he could split the account 5 ways and we'd all retain VIP platinum (which is not true), others would try to sell him more so we could all have enough to be VIP platinum on our own). Salespeople have no clue, and quite honestly, I don't think anyone in Wyndham titling does either. The best advice as far as putting in a trust or not is to talk to an estate planning attorney. But there again, timeshares are confusing (doubtful an estate planning attorney will understand you need to change the recorded deed AND do a transfer within the Wyndham system).
I like Jan's suggestion to put the developer point stuff in the trust, and not worry so much about the other. Any resale stuff isn't worth much on paper anyways, so why worry much about probate? The stuff of value is the developer points so protect that. Then again, we're the only ones who really know the value and difference thereof between developer and resale contracts (how would that conversation go in probate court?. The thing I learned enough about to help guide our decisions for my father and my siblings, was that it was important to keep the developer stuff together and never split it up (so it won't lose it's VIP platinum). We each said we're in or not, and if not there was no monetary compensation - because split up the platinum account becomes worthless.
As far as transferring an existing contract into a trust, I do think you need to do both parts. 1) Update and record the deed 2) Send updated deed to Wyndham title and have them complete the transfer on the Wyndham side. A reliable transfer company, like LT Transfers often recommended here on TUG, would facilitate the whole process, I'm fairly certain. They have handled transfers (purchases) for me in the past. After recording the deed, they sent the information on to Wyndham. LT Transfers advised me when it was complete.
If you have an existing contract, say under Jane and John Doe, when you book a reservation, you'll put Jane Doe or John Doe as the guest. If you transfer that contract to a trust, the names would show up as Jane Doe, trustee or John Does, trustee - when you select the name for the guest on your reservation. The resort doesn't care if your reservation shows Jane Doe or Jane Doe, trustee, they are going to check you in.
If you have updated and recorded the deed so you are now Jane and John Doe, trustees, but in the Wyndham system you are still seeing only Jane and John Doe as the owners, you won't have trouble booking and using your ownership, no one is the wiser. But come time to sell or transfer to another owner, I suspect Wyndham is going to want their system to match the recorded deed. Since this is all so confusing anyways, to those of us that have some clue as to what is going on, one can only imagine what it'll be like for a newby trying to wade through this stuff. So, IMO, having the recorded deed and the Wyndham system aligned property is the best thing to do. Sadly it'll cost big bucks, as far as I know. Ovations (legacy or tribute or maybe now it's call Certified Exit) may waive some fees for family transfers, I'm not clear on that. But my best guess is they'll first want to align the recorded deed and Wyndham account first.
My best guess. The only rule with Wyndham - you do the best you can, make your best guesses, and then see what really happens. Things are not consistent, processes aren't well defined, and they may handle it for you without charging, or handle it later for without aligning, you never really know til it happens.
For me: All developer contracts are deeded in my father's trust. He already had them set up that way. I have one resale contract in my father's name and mine (yes they will link a John Doe, Trust contract with a John Doe contract (puts everything in one Wyndham account). The remaining resale contracts have my name and whomever I wanted to add so they show up as owners. I honestly have quite a mess and need to document better how one will get rid of all this if no one wants it. I hope some of it could be sold resale for some profit. But also rely on Ovations to take things if people don't want to mess around with it and just want to walk away. My kids want nothing to do with it, but I have a nephew who I suspect may take it over some day. Trying to position things so whatever needs to happen, can, with no financial burden on anyone and hopefully family will continue to use and enjoy it for many years to come.