Ditto, I use PriceLabs for my STRs - here is a nice writeup ...Airbnb Smart Pricing Vs PriceLabs: An In-Depth Comparison For Hosts | Boost Your Short-Term Rentals

I am guessing that the tenant may be short on funds to pay twice for Jan, until reimbursed by the old owner, so would first make your case to the old owner who has the funds you are owed and certainly hope once reminded of that will refund them. 

Currently, we manage approximately 40 short- and mid-term rentals, in addition to a few long-term properties.

In 2019, I launched my own revenue management agency to help Airbnb owners boost their income and achieve greater returns on their short-term rental properties.

And if your investor friend’s private loan helps fill in any gaps, it might be worth considering that short-term pain for long-term stability.What do you think you’d focus on first... paying off that line of credit as fast as possible or jumpstarting the renovation to boost cash flow right away? 

If it's on the higher side you may want to consider it for mid-term or long term rental, but if most stays are below 30 it can be viable for short-term! 

Short of coming here and meeting face to face with them and come to a couple local REIA events to discuss, for those who are remote I would suggest getting into some of the NE Ohio REIA facebook groups to get some advice from locals.   

I do stocks and all but real estate mogul stuff fits me better.

I'm looking to build a Casita/poolhouse for use as a short term rental in Summerlin.

I’m also based here and have experience with short-term rentals, property management, and work with investors like yourself.