An easier route would be to convince him to go in on the short term rental together in a partnership. 

They have a bigger single family home and a tiny home on the property, but there close proximity and shared driveway present functional problems that are undesirable for guests. 

This deal not only demonstrated our ability to execute rapid flips but also underscored the value of our strategic partnerships.

You will need an attorney to properly structure the partnership and you will make sure you do it correctly.

Our property was already functioning as a short term rental so it is furnished but they are getting rid of some of our furniture and putting in new furniture and they are just charging me for the removal of my items.

We get inquiries all of the time on Airbnb/VRBO/etc for large group functions at our properties, even if we say in the listing it is not allowed. 

this is unacceptable for someone like me who manages and is a member of multiple separate LLCs, partnerships, portfolios.  

Consider using DSCR loans- Cash flow of the property is considered in lieu of your income3.Consider purchasing in a different asset class (Large multifamily) where borrowing will be a function o fthe property income, not yours

If you're looking for software with strong rental accounting capabilities though, there are apps that have this functionality built into them (rather than paying extra through RentRedi to use the REI Hub.

@Gustavo Delgado I've looked at stocks, bonds, REITS, limited partnerships, and syndications, and have invested in all of them.