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I would never hold a reservation for anyone unless I know them personally, they are a repeat guest or I had a special request with a clear reason for doing so. The guest gets a notice that the room is not being held for them. Whoever books first with payment gets the room
Pre-approvals go to anyone who is a good fit and it’s okay to give as many as you like, even for overlapping dates. I hesitate to even mention other people are looking at those dates because it can come off as a sales tactic. Since I also have IB, anyone can book before a pre-approved person and I wouldn’t even know.
I had one lady spend 4 days going back and forth, with 2 expired pre-approvals. Someone IB’d the dates while she was farting around; she wasn’t pleased, but the reservation goes to whoever puts their money down first. After some learning experiences holding dates for people who flaked, I only hold dates for returning guests or longer bookings.
I haven’t tried booking on other sites, but mostly because VRBO and Travelocity seem more geared toward whole house rentals and I have a guest suite in my house.