If the complex already has it, you should be able to keep it (you will need professional management and the ability to check all the other boxes).  

This will greatly affect my ability to pick up commercial lots.

They will look at your ability to afford it--having a rental lease in place helps your financial picture, which is why BRRRR advocates have the "Rent" before "Refinance," and they will typically do something like 80% Loan to Value (LTV).  

One other important element to consider here is that if you need the rental income from the property that you are leaving, then FHA will require that property to have 25% equity. 

The best argument for the traditional agent in my opinion is that some individuals have the ability to be in the deal flow, have good relationships with vendors, lenders, escrow agents etc. and know how to negotiate on behalf of the client.  

AppFolio also has the ability to provide access to reports, and statements directly through an Owner Portal.

Ability to split roommate payments?

They have the ability to use that towards qualifying you for a mortgage.

If you do have the ability to move into the home then you should.

My opinion is they can both be profitable and cash flow...but if you have the ability than sweat equity is where it’s at.