And let's not forget the ecosystem that supports this—realtors, property managers, cleaners, photographers, stagers, etc.Let's keep this conversation going.

This will be hard if he intends to keep the property as he will not want to pay you full market price.The main point is that you need to make sure that both sides are comfortable with the arrangement up front. 

I would keep your peak season pricing the same and look at improving the rest of the year by decreasing pricing some until your occupancy rate ticks up a little.

I would love to see this happen. keep me posted please.

And I'm sure you know that northern portion you are in is a great place to be as well, it's just more challenging with the prices being higher sometimes those rents don't keep up as well. 

but it's in an A-class area and so i'm keeping it.hope this helps. 

I would make sure you keep a contact log of each time you've reached out and how long they took to respond. 

A permit had to be pulled for electrical, plumbing, and an egress window has to be installed in a bedroom.Honestly, I would just keep renting it out as is and not waste the money or resources on trying to convert it

Depending on your amount you may want to consider a debt fund too as its less work and your money is deployed/paying you interest so you do not have to keep finding deal after deal. just some food for thought

The reality is, it's not going to last.Only those hosts treating this as a business and offering the best product are going to keep both rates and occupancy high.