thanks everyone @Edgar DuarteI would suggest you research “return on equity”.  

Quote from @Keegan Darby: Hi BP - I’m seeking advice on a property I own. 

Spend at least 2 hours per day researching online about your desired investment strategies.

But in general, your biggest risks are not necessarily what's the maximum rent you can get, but can you find a reliable tenant that will always pay and pay on-time.

Those that cannot weather the storm get wiped out.Having cashflow positive properties provides a margin of safety you just do not have with negative cashflow.Why are you focused on buying in your backyard? 

I have been working with investors in my area and partnering on deals for the last 4ish years.

Staff often seemed to focus on one requirement at a time, and only moving on to others as each was taken care of, instead of starting them all at the same time.

I would only underwrite based on actual rents not proforma.

I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

Welcome, best of luck on your journey