There are some ways around the blackout dates. From the Wyndham website:When they added blackout dates previously, those who were already fully booked were grandfathered in and not in danger of getting bumped. However, fully booked means that the owner has already sent the renter's name to Wyndham. Some owners take their time sending in the name (possibly for good reasons dealing with refundability or such). I would not expect the January 29 weekend to be added (January is a slow period for travel to Orlando), but then most people were surprised by the other blackout dates. It could happen again.
"You can travel with your guests to these resorts during the dates listed below and may use two guest confirmations per year during the restricted dates when not travelling with your guests."
The key thing is trusting that the person you are renting a reservation from knows about the Wyndham blackout rules and knows what they are doing.
The blackout dates and rules are well-known by the people renting reservations, especially those doing it as a business. There may be a smaller owner that rarely rents that may not know, but I think that is unlikely.
Of course, It doesn't hurt to ask if you are renting during a blocked-out time. You want to be confident in your reservation.