She is well established and is recognized as one of the top investors and brokers here in the Indianapolis market. 

Even though there were tax implications, I think it will serve me well in the long run.

You need income to qualify for loans, you can learn how to manage rentals well (something most landlords never do), you will figure out which communities/properties make the best investments, can earn an above-average paycheck, and may even find some investment properties before they hit the market.

I used Asana as well

Great question - when you find out let me know as we are looking for one as well. 

Personally, I invest in properties in C-Class neighborhoods in my market (East Linden and Southern Hilltop), and they’ve been cash-flowing well so far.

The hilly terrain is a main reason for this and you can't really see that on a map so knowing the areas is key.We have old housing stock as well so big things like plumbing and electrical can vary cost wise if they have or haven't been updated.

Ryan, I appreciate your insight as well.

Id like to enjoy another stream of income to eventually phase out my day job, so that I can focus on acquiring commercial properties as well as a business or 3.  

don't be afraid of better markets in ohio like columbus. depending on the capital allocation buying old houses and having to renovate is not the only way to drive value. build rent refinance repeat and build to rent are both very strong market drivers as well and you can traditionally get infill land in areas like columbus in much better locations than where you buy.