I remember reading a book several years ago about an investor who specialized in this  (it could have been this one: "Swapping Real Estate for Fun and Profit"), but I need something a little more specific. 

My net profit would be equity + monthly "spendable" cash to spend or use/save towards another home.   

Using hanging bags and postcards + business card.Intend to start writing content for longer term free SEOIntend to solicit local RealtorsIntent to start our own meetupWhy We will use initial profits to pay for additional marketing (currently coming out of pocket) and to replace cash on hand for next flips making us less reliant on hard money and more able to more quickly acquire (no need for appraisal).

I currently have about 100k equity there.2016 capital gains income: 02016 business / gambling income: 25k2017 capital gains income: 152k2017 business / gambling income: 28kChecking account balance: 100k+Credit score: 730Investment property price range 165k - 200k.I can get letter from CPA stating I've been in the same business since 2010.I'm being told they will take either last three years of capital gains or last two years of gambling. 

However, when we do our calculations, the property in Waco seems be more profitable in terms of cash flow.

I made a nice profit for SXSW this year by using Airbnb.

Not familiar with your term, "house hacking" but I'd recommend picking a few ways to learn and profit from real estate.

With those type of tenants, and the age of the property...is it going to end up being an ongoing headache that will nickel and dime away the profits?

If you sold it can you break even on the sale or show any profit.

We didn't make any profit on the house but we did gain valuable experiences.