Long post......sorry I got carried away with IT speak.
I am going to reserve opinions on predicting the how these Wyndham change impact future booking patterns.
The auto upgrade might change the way some people behave, but not all. Some will still try to game the system, some will not. It obviously depends on what you usually book and what inventory levels there are there. It also depends on exactly HOW wyndham implemented the feature in the new system. And Wyndham at this point for me is the UNKNOWN.
I think for those who usually play the cancel and rebook game, HOW and exactly WHEN the system processes cancellations AND automatic upgrades will determine what people do. If it is real-time, than that C/R game will NOT work if there is NO inventory available when you do your C/R, as your cancel will likely be someone else's upgrade, especially during high demand time. I think if Wyndham is going to cut off this C/R game, they would have to make it real-time (with business logic to figure out if an outstanding upgrade request exists), or at the very least NOT return canceled units back to inventory immediately and then in some regularly scheduled batch jobs, match canceled units with outstanding upgrade requests. Since the new system is suppose to be 24/7 there is NO overnight processing window. So its Realtime or it frequent batch jobs. So in either case the canceled inventory either NEVER returns (matches an outstanding upgrade request), or the inventory returns, but it is DELAYED (no outstanding requests matched, but inventory is returned once matching batch is run). Doesn't help those who use C/R as a general approach.
However Wyndham IT in the past has not been known to be the A team, so this new auto match feature might be a bit much for them to implement thoroughly (by my business rule and IT standards). They may implement something they think will work, and deliver on a promise, but we may find a work around it. To make system processing simpler, they may have just implemented a batch checker for upgrade processing, they schedule it at off hours to not impact overall system performance (because performance matters). And in Batch mode it checks outstanding upgrade requests against current available inventory, upgrading where matches align. Remember the nice brochure said upgrades IF AVAILABLE, it did not say it was delivering a VIP status based + booking number (they are generated sequentially, so lower is earlier) priority upgrade. So in is most simplistic terms, if Wyndham runs a batch once a day or hourly and checks available inventory against upgrade requests then they are delivering on what they advertised. Now this implementation is not as smart or as sophisticated, nor does it take inventory as it becomes available and offers it first to those who booked first, but it is easier to implement systematically. Less real time rules, or less pending cancel or pending upgrade status of inventory (like they need more states inventory can be in). So if they took the easy route, we may have a chance to still use C/R (that is until they hire me as a consultant or someone in IT reads this posting). If they implemented this latter approach, I suspect it may be a short term implementation which eventually they will remedy, but in the meantime C/R will still work, provided you do it in between batch jobs. I honest doubt that Wyndham is this stupid, but they have proven me wrong before.
Now since 90 % of my bookings are within 60 days and I do take advantage of WHAT is available in inventory and don't rely on a C/R approach, this will impact so little I likely will not care. I am using the VIP perk as intended for excess inventory. For the 1 or 2 bookings a year that I do a SRP, it would be a nice bonus to get a free upgrade on them, if it happens. So on the whole it doesn't bother me, as my approach to utilizing my points is not predicated on the use of the C/R approach.
I understand other have bought into that approach from sales. But I have always understood that all rules including VIP can be changed and altered and I suspect when we find the next work around they will change business rules to curtail that activity too. Remember not so long ago we could transfer points to another member, I have unlimited GCs at a VIP Platinum member, etc etc. All I know is change will happen, Most I can live with, some I don't like, but I work around it my just changing my behavior. As VIP Platinum we used to have unlimited GCs, so in that case, as soon as I make the booking I put on GC, because I didn't care if they canceled and it did not cost me. Then they implemented a limited number of GCs. So now by behavior is to wait until almost the 15 day mark before putting on the GC name, because if they DO cancel I don't want to burn a GC. If at the end of the year I have some left, I put them on as many as I have known bookings for in the next calendar year. So now with new change, multiple reservation must have a different name, I will just alter my approach again.
As Ron said, it is just a constant evolution and adaptation. You just figure out a new norm and new approach and then keep moving on. For some the answer might just be to bail, as the change is too significant or you just can't get over it. Up to you. Life is too short.
So we can hope for something but expect whatever we get, it will change.