My condolences on your loss, JAB. What a lot you've had to deal with, in addition to your loss.
$9000 is not a lot to pay for a VIP Platinum account. Is it about a year behind(?) and if you paid it up you have at least 1.6M points to use this year and every year (of course paying ongoing maintenance). Are there additional points credit pooled or deposited? Getting paid up and having access to your points - IMO - you could recoup the $9000. A lot to take on - but perhaps doable.
I have my Dad's VIP Platinum account - he had about 1.4M points which I now manage for my family (we use it for vacations, and I've made some money renting the excess). I had the luxury of baby stepping into it - learning the ropes bit by bit. I "took over" when he paid someone to "take it off his hands" 5 or 6 years ago. Thankfully he was able to cancel that transaction, and here I am. NO regrets keeping it thus far (other than Wyndham can be beyond painful to deal with and can and do change things on a regular basis). Eventually I supplemented with more resale points. Again, baby steps. Another consideration is that Wyndham has drastically changed things up this past year, renting excess points will not be as profitable as it used to be, but I still am thinking I can keep this going.
I can only estimate that my Dad paid $150K - $200K. I'm assuming you inherited this from your parents and very likely they paid that much as well. This is my inheritance, I'm not willing to give it away.
Last I checked, I can give mine to Wyndham (Ovations). I estimate if I sold Dad's 1.4K, given the properties they are (aver. MF is $6.5/1000), it would bring $15K or so (versus giving them back to WYN).
VIP Platinum IS nice. The people with resale, paying pennies on the dollar for their points, likely pay (substantially) more for their vacations than a VIP Platinum. They pay full points for their vacations, unless the resort is offering deals (some do, I don't ever pay attention to that because VIP Platinum discounts are always better).
I look at as - pay upfront - be VIP - and get discounts that (over a REALLY long period of time, and likely never) pay for themselves OR buy resale - get in cheap - but you will always pay more for your vacations.
My long winded point is that you have something that is worth some money IF you want to learn to use Wyndham (or perhaps pay someone to manage it). You could use some and rent some. My Dad was concerned he was giving 'the gift that keeps on taking'. I do not feel that way, I am beyond thankful to have this (but I'm crazy and obsessive and actually enjoy managing this for the family and the rentals on the side). It has been a good thing for me.
You may also want to give some of the contracts back to Wyndham (the higher maintenance fees ones) and keep (or sell) the better ones - assuming all are VIP eligible. You should be able to pick and choose what you keep. Keep your point total over 1M to maintain your VIP Platinum status.
Your situation is my husband's worst nightmare, BTW. He listens to me as I talk about the day-to-day challenges with Wyndham. The conversation quite normally ends (somewhat serious, some jest) with him saying, just be sure that if I anything happens to you - I have the phone number for Ovations. I like to think one of my nieces or nephews will take it over, a couple are interested and quick studies. My kids are not interested in managing it whatsoever.
Best of luck to you. As you can see, you'll get a lot of different opinions/advice here. Some that have posted I don't think are Wyndham owners, those that are may not be VIP, something else you may want to consider.