Also, many lenders are picky about the operating agreement and structure of the LLCs.

I also own a short-term rental management company that partners with other real estate investors and second home owners to 2-5x their returns while also taking the headaches out of operating STR’s.

You could use a simple move-in checklist or form for them to document any immediate issues.

@Nick Belsky gave you great advice.In this situation, best to keep it as simple as possible, and I often give two offers; first, perhaps an all cash (way below market) and let the owner know that it is what it is--a below-market offer.#2 would be the seller holds the financing--I wouldn't go to a 30-year amortization, especially with an 80-year-old seller. 

For that reason I built a full-functioning cash flow model taking into account hard money, the mortgage refinance and all relevant operating expenses to assess monthly cash flow.

It can be a simple 1-2 page Option contract.

A simple check-in during their stay shows you care without being intrusive.Implement Self Check-In: Guests appreciate flexibility.

Here are a few simple and free ways to learn: Go to real estate meetup groups, attend open houses and speak with the agent there, inspect FSBOs (for sale by owner), walk your area, and speak to people tending their yards.The idea is to engage with other people and ask, Ask, ASK questions about their experience with the local market.Some other ideas: find a home inspector who will let you tag along in a property inspection, and absorb what they are looking at and why.Your mindset and enthusiasm for learning about real estate will open many doors for you.Good Luck!

I would love to meet some new members, young or no, whose goals might include a solid cash flow and providing good value to renters who are exploited or poorly treated by unresponsive landlords or large corporate operations.  

We've been communicating quarterly on the property status, but a simple search on Zillow made me think he's lying to me.