Vacation Rental Under Contract - Transfer VRBO, Sales tax, etc

[Keith Schulz]

Hello All,

I see a discussion from about 3 years ago on this topic, but VRBO keeps changing things and regulations keep changing, so I thought I'd start a new discussion.

I have a vacation rental property under contract in northern Wisconsin, closing May 28. I've got experience in long term rentals and flips, but the vacation rental thing is new to me (because what else do you do during a pandemic but start a new business). The current owner has several bookings lined up for the summer, but has canceled March and April and May due to our "Safer at Home" orders. All of his bookings are thru VRBO.com. VRBO tells us they can't transfer bookings from one owner to another. It sounds like books need to be canceled under the current owner and re-booked under the new owner. So what is the best way to seamlessly do this? 

I'm planning to start advertising thru social media to try to line up more renters for the coming months. I think people will be ready to go somewhere as soon as the stay at home orders are lifted. Should I just have the current owner block out the times that new renters would like to stay? Do I start a new VRBO listing now, or wait until it's officially closed? What other places should I advertise?

Can any vacation home owners enlighten me on how sales tax is done? I believe I need to get a permit to collect sales tax?

What are your thoughts on entity structure. The financing will be in my personal name (it was the cheapest easiest way). However I do have 3 entities currently setup. One is for my long term rentals, one is for my real estate brokerage, and one is for our sales as agents. I was thinking about lumping this one in with the long term rentals or just leaving it as a sole proprietorship until we get things rolling and figure out the best path. 

Thanks,
Keith