My view is there is more protection on a wrap than a sub to and with the right disclosures and underwriting can be an alternative option. 

He spends every waking moment in the field, making sure every seed is placed perfectly.

There are those on YouTube who are very close to violating the law, if not dancing all over the line.In my opinion, the real problems originate when the buyer isn't clearly disclosing the risks to the seller, or violates the Consumer Protection ACT, or doesn't have enough capital to make the payments, or does equity stripping, (some equity stripping is legal, some is not)  12 U.S. 

I've heard there's a good chance the mortgage company won't care as long as the payments continue to be made on time but I still want to protect myself just in case.

You will be spending 350-400K for a duplex.

For your sake I would make sure, if you aren't NNN right now, that you at least have RE taxes protection in your lease.   

My Name is Miles, currently living in Arlington (DFW Area), I've always had intentions of at some point getting into real estate, now at 40, and finally at a place financially that it is feasible, I'm planning on spending the next 6-8 months learning all I can (and then rest of my life continuing learning lol) before taking the FIRST plunge.

You can then set it up to where they email you when a house comes on the market that meets your criteria (let's say a multifamily house in a specific zip code that has been sitting for 90+ days) so that you aren't spending a lot of time looking through listings that aren't going to get you anywhere.

If I could deploy the same amount of up front cost to purchase an up and running portfolio.My calculations tell me that I can be cash flowing much more if I spend the money on a portfolio or complex.

Be prepared to spend a ton of dough.Personally I think that it is unnecessary.