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Yes, you can keep the reservation even after you sell the week.
Yes, there are risks of losing the reservation? When I purchased one of my SVV units a few years back, I could see the selling owner's reservations even though I had first use the following year. So it is possible -- I'd say Vistana's IT systems and processes were not stellar at the time. Maybe they have improved... but I honored the terms of my sales contract (as I should have).
I'd say why not just wait until May or June to post the unit and sell then. By the time you find a buyer, it will likely be July anyway and your reservation will have passed. First use is 2021 and I don't think it will make much of a difference. You can even make a home reservation for the buyer if they so desire and it should transfer.
Of course, you could just make sure it was clear in the sales contract. But what happens if your reservation is cancelled/altered? You would have to likely go back to the new owner and might not get the reservation back -- maybe you get Vistana to help, maybe you pursue them in small claims but that is costly... if it were me, I'd wait until the reservation has passed.
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