Well I've been doing this about 4 times longer than you if that is your measure. 

Make sure security lighting is good at night as well for safety of your tenants, to prevent illegal dumping on your property, and for helping keep illegal activity from happening in your parking lot ( drug deals ) etc.No legal advice given.        

And when I say dive in...I literally mean no safety net or wings.I will just shoot for the stars.That being said.

This is important for a number of reasons, your safety first and foremost, but the other simplest reason is the balance of energy to the group dynamic at the meet.  

I'd warn you to not reveal that you're the owner for your own safety and I'd suggest for you to be as hands on as possible to learn as much as you can!

My hope is that the same contractor can inspect not only building safety and structural soundness but also perform lead paint checks, termite check etc. 

I love the country and its people, but it's still very much a developing nation, and living here is definitely riskier than in first world countries.Our local currency - the Rand - has taken quite a hit in recent years, and with the emergence of the Economic Freedom Fighters (a far left political party, who basically want to nationalise the economy), I reckon it's a good time to look at investment opportunities overseas and establish a bit of a safety net for our family.For now, I'm specifically interested in turn key investments.

I visited a property in Chicago that I am set to close on in a couple of weeks to get some measurements.

This is something that you can easily measure when your looking for your house.  

(Since we're house hacking I want to make sure that we don't have to deal with safety issues.)I'm obviously hunting for value here but I'm willing to pay the Lakewood premium for value that surfaces in the form of quality of life.