Sun goes down you won't be having as many strategic conversations with your passengers.

You'll also begin to get a feel for how other markets behave and what marketing/buying strategies may work for you.

Considering you live there, my first step would be having a talk with the guy.

First sign of trouble, you should be having a sit down and set your expectations. 

Will you be having another investor lunch meet up?

I would say it is best to buy your first few properties in an area you are familiar with, specially if you will not be having a property manager.

Something you could possibly do would be have a home inspection done for ~$500, and that way they will be able to tell you anything that might need addressing now and in the future for peace of mind.

You must be having a lot of success with the crowd funding :)@Jon Klaus Unfortunately, the numbers are too tight with the existing structure.It comes down to taking the risk or walking away it sounds like.Can you think of any reasons why someone would be reluctant to sign a demo permit if someone else was paying for it and there is no risk associated?

I have entertained the idea of buying a multi-family residence (duplex-triplex) but the down side for us would be having to share walls with tenants.

Understanding the numbers is easy, they behave in predictable ways.... people not so much.