Renting to your friends will just put you in a compromising position where you are forced to make inappropriate business decisions based on emotion rather than the most financially responsible way to run your business. 

Go with the info always and leave your emotions and heart on the side line.

Do remember to treat it as a business and remove your emotions from "your space."

After running skip traces and finding some properties with deceased owners or owners who are listed at 117 years old, what are some things I can do to dig deeper?

It's hard to judge emotion through a text message, but the response was pretty huffy...

Best to not get so emotional and attached to a property - easier said than done right? 

For those afraid of needlessly spending more money than they have to; consider getting a basic inspection, and then ask the inspector whether they feel there is any value in deeper inspections or not.Choose a reputable, unbiased inspector.

I'll connect with you guys and we can dig deeper.  

Gives me a pin at each address and then the pop up shows me unit count and sales date which helps me decide if I want to dive deeper and find owner info

I always feel for the person who inherited a property-the situation can be really emotional and the last thing a lot of people want is to go through a rehab process while grieving.