Hey @Anthony Dupre, whatever you decide for your entity structure, ensure it's simple enough for you to easily abide by the structure in your day-to-day operations.We've had bookkeeping clients with complicated structures that apparently protected them to the maximum degree but they didn't abide by the structure when conducting transactions in their business daily (lots of unintentional commingling).

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

Its super simple.

@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. 

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.

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

Thanks Yes simple, you have it inspected by a led cirt guy, 500 per door.

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!

Stuff as simple as replace cabinets/counters and repaint.