What are the largest pitfalls one may run into that turn this from a 150 to 350 ordeal?

That's $1680 per year for QBO, plus my Bookeeper at another $500 a month to log monthly statements, break down loan payments, and reconcile.

Well anyone can write anything into a contract, but whether it is legal and enforceable is for the courts to decide...It is State law here that a contractor must call 811 or they are liable for the costs.

Would you rather her destroy your property, your insurance deny the claim and you're out all that money you just put into the rehab?

So you would either need to learn a lot about how to be an awesome STR operator and you would probably need to put into your home $20,000 to $100,000 in adding furnishings, design, and adding amenities to make the property desirable.

As for Raleigh, if you’ve already seen the success of Airbnb-ing rooms there, it’s worth exploring further, as it’s a growing market with plenty of demand.For alternative strategies in Greensboro, look into renting by the room, especially for professionals or students.

@Robert Brock, I guess my advice is not really any different than I would say to someone wanting to be a residential wholesaler: you need to add value to the transaction.Often times, having the deal tied up is the value, but more often then not, in my limited experience with commercial wholesalers and residential, the wholesaler has no idea what someone will actually pay, so they tie up a deal at too high a price and then add their fee that turns a bad investment into a horrible investment. 

But I don't know that I would jump into real estate just yet either.

I put roughly 20% down on a $200k home, and am curious what steps I could take to possibly turn my original investment into a large portfolio within the next 10 years, when we're currently "low on liquid funds" after finishing up a wedding.... 

That would be a separate mortgage and not what amounts to a second loan on your personal residence, which if you have spouses, they might not be that into.