Basically saying that good liability insurance will do the trick as LLCs are easily pierced and just complicate the lending process. 

Basically everyone helps where they can but the official PM has to be my step dad for those properties because he is the owner. 

Yes it's done all the time it's basically a live in flip under those circumstances.That's assuming you mean selling it after a few years once you've captured appreciation.Otherwise you could keep it as a rental and then refinance your equity out to buy a second property.Also worth noting as long as you live in it for 2 years you'll also get the $500k Home Sales Tax Exclusion.It's really just a matter of if you, your wife and one year old want to deal with living through rehabs.

I'm basically trying to make sense of the big picture. 

They know the basics, but not enough to help you really know the local ins/outs. 

So I was able to get someone to meet the tenant at the property for the keys and to basically do a quick walk through to makes sure there was nothing major going on or left behind.In my state, TN, apparently, if the tenant is present for the final walk through then the landlord has to give the tenant right there on the spot a list of damages that would count against their deposit. 

Basically, if you were us, what might your approach be to breaking into real estate?

Thanks James, that is basically what i have been thinking

Since this is my first multi-family property, I really don't know what questions I should be asking or what information to look for aside from the basics (construction issues, vacancy, etc). 

Before I retired, I was a broker, residential/commercial RE appraiser, expert witness in State and Federal Court, and a professional RE investor.