One property is about 3 acres that my main house is on and the other is just land with a well on it and it's about 2 acres.

In some submarkets, properties are moving very well and there is appreciation even in that price range.

Your interest rates are often higher for a non-owner occupied home  than for a personally owned home as well.   

It's not unusual to see 3/1 and 4/1 Section 8 properties but that single bathroom would not do well as an MTR.Overall, I'd say location and the shape of the property is going to be your key driver and the factors that will make or break you in the MTR space so very carefully evaluate both before you make your decision. 

I started on house hacking as well when I moved from Portland OR to Columbus OH to start with real estate investing and grew my portfolio to over 7 figures.

As you know, we have been flooded with STR's up here in the last few years.

The other option is to try and bring on another partner as well

My thought was to 1099 the friend for her part in the projects, as well as assess how the dynamic is working between projects. 

I have also looked extensively into Cleveland as well.

The strategy that works very well is they use their VA loans to buy a 2-4 unit property, and live in one unit and rent out the rest.