This is the kind of situation where you absolutely need to get a local real estate lawyer involved.

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’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. 

Also, trying to have a hands-free airbnb business seems to be especially hard. 2.Team Up with Experienced Apartment Syndicators:•This option involves partnering with a small group of experienced apartment syndicators to focus on acquiring and managing apartment buildings.

Would there be gift taxes involved as well?