Larger deals can be done via syndication, which has strict SEC limitations you would need to abide by. 

In preparation for that, I am trying to find a good way to manage preventive and routine maintenance. 

If he was truly licensed then he knows the routine and should know better.

Also, find out ahead of time what closing expenses are routinely disallowed.

strictly buy and holds?

Also VA loans have strict requirement for properties so it wouldn't be easy to find a house to flip that they agree with.

Research is very important so you have the right routine.  

These are only some of the questions you need to think about now.When I started, I wanted to be an investor friendly agent, not strictly a residential agent.  

Personally, I would sell it because it isn't performing stellar when you factor in capex, routine maintenance, vacancy, and management, then I would utilize the proceeds to acquire a better performing property, like a small MFR.  

When they are sold on the secondary market the big banks have to adhere to strict loan requirements to do so, therefore, they can't be as flexible with you on terms.