My wife and I have a child in elementary school so we don’t want to share our living quarters with strangers, and most multi-family properties here are either way over our budget or less quality of living than we’d prefer.

If its a stranger or a company, its hard money.

Everyone I have seen who says investing doesn’t work are usually fearful of making offers or talking with strangers.

Even with strangers, distressed homeowners, etc, it seems like a win-win.  

He doesnt want to rent it out or sell it to a stranger because it is a family home.

When we show up we're just some stranger who drove there.

Investorinˈvestər/nouna person or organization that puts money into financial schemes, property, etc. with the expectation of achieving a profit.If I'm a grieving widow/family you're coming across as a stranger who knows too much about my business and is attempting to turn a profit off of the death of grandpa. 

I always recommend that people hire an attorney to draft legal documents rather than sourcing them from strangers on the internet.But it seems like it’s just a basic rental contract with a clause that specifically allows you to sublet the property.

Do you think its odd that an employee would be hesitant to say too much to a stranger about another employee?

We are drawn to people who look like us.If you put 50 strangers in a room and three of them have sleeve tattoos, guaranteed those three people will end up talking to each other.