LLC is going to give you legal protection to some degree, but there is no difference from a tax perspective.

The only way I thought I could protect myself better in this situation if I were to decide to move forward would be to cross collateralize by taking a first lien on a separate property of the borrower.

I get the concerns about liability and title insurance, but I’ve had success by thoroughly vetting the company’s history and securing protections like hold harmless agreements.

Not necessarily for tax purposes, but for asset protection purposes.

I hear a lot about standard personal loans, mortgages, etc - but do banks or smaller players consider situations like the above?

I was able to get proof that my properties are on the up-and-up for lead levels, if I were to have had lead issues, it would have been a lot easier to address and remediate them while my properties are vacant vs occupied, and I'm protecting myself as an investor from potential headaches if the city does in fact start to enforce having this certification prior to evicting a tenant. 

If the two are afraid for their well-being most places have laws in place to protect them by letting them out of leases-given it is usually women escaping domestic violence.

If he wants to retire I would definitely play up the continued monthly income side....You might also be able to get him to see that a lower interest rate protects him from a refinance out. 

They have no authority in the county run areas and if the county changed their rules they would run afoul of state protections.

@Scott Trench Had a deal close last month with a combination of your scenarios/players.