If you decide to entertain this, due diligence will involve digging deep into the business financials to understand cashflow, solvency, and liquidity, his personal finances, and searching for any liens or UCCs in place. 

I recommend buying it under your personal name.

Thats more like a temperature check on how optimistic everyone feels right now.Any long term prognosis can only rely on supply and demand projections.

@Rich Schmidt I know the feeling.

When the first type of person chooses to self manage, they generally have a great experience, and they also get to pocket the extra 20ish% that they would pay if they hired someone else to manage their STR.

Rents accelerated at unprecedented amounts, more multi family built and now here we are at this time feeling the effects of rents stabilizing and experiencing higher vacancy.

With buying a home for personal use, what are the best months of the year to purchase where the cost will be lower.

I personally think networking is your best route.

I have a tenant that is going to be evicted and i don't want them coming back saying that I withheld any of their personal property, so trying to prepare and have something prepared for a final walk through. 

Feel free to reach out if you have any other questions or if you would like to discuss!