A house hack involves living in the property which means it's somewhere where I (more importantly my future wife) would be willing to live.

Zoning ordinances, building codes, and ADU rules are all hyper local, so I would suggest you get an architect involved to help sort through everything.

You can have companies meter them individually but being in DC I thought it would take too much personal involvement.

It involves establishing a clear vision for your company, determining how you want to differentiate yourself from competitors, and asserting your unique value proposition.

However, it involves more management and higher stakes with multiple properties.

I told my tenant that the contract is between us and as long as she pays rent on time through charity or on her own, I don't mind but I do not want to be involved with a third party.

We started off on a good note with the tenant, he paid his rent on time, and so we didn't have a real reason to get too involved.

I assume that is where a good portion of the variance is coming from.Great job diving into the numbers on the properties as that is always good practice and allows you to better understand what numbers you want to input on the various types of assets you explore investing in. 

I’d like to build a team and have a property management company involved that way I can utilize my time and efforts on other things besides maintenance. 

If you decide to entertain this, due diligence will involve digging deep into the business financials to understand cashflow, solvency, and liquidity, his personal finances, and searching for any liens or UCCs in place.