My wife and I have obtained three traditional loans and one lease with the option to purchase, resulting in most banks turning us down based on debt to income (non-portfolio lenders). 

--reach out and thank them upon getting the booking and ask if they have any questions--send a "Welcome" email or automated message during the week prior to arrival--reach out the day after arrival to ask how everything was the first night and ask if there is anything that the property needs--reach out at the end of the stay (that morning or within 24 hours) and ask how everything was, anything to improve, anything to add to the house and then offer an incentive for returning guests.My 2 cents,Mike Absolutely stay in your place as Mike said.You will see things the cleaners will never let you know about.We stayed in our PF will putting up the Christmas decorations and found a cracked plastic shelf in the fridge. 

From what I've been hearing it's approximately up to 3 months to place section 8 tenants there but the leases can range anywhere from 1-5 years.

Originally a 30 year lease, theres about 20 years left to an advertising agency. 

Creative ApproachesIf the organization is hesitant about a sale, consider proposing creative terms:Seller Financing: The non-profit could retain an income stream from the property by financing the purchase.Partnership or Lease-Purchase Agreement: Offer to lease the property with an option to buy, giving them time to evaluate the relationship.Donation or Support: Consider including a donation or offering support for their mission as part of the deal.

Here's the issue...in most states, if the tenants have a lease, the new owner will be obligated to honor the lease - as is - until end of lease. 

Currently you have a STR lease and can effectively move anywhere the job market takes you.

I would terminate this lease ASAP. 

But if you're holding long term with no plans to sell in near future - better to get them leased up!

Finally, the insurance provider repeated their answer, and this hurdle too was crossed.Very early in the process, we sent over leases for our rental properties.