Do you want this thing to be the tipping point for them to leave and you have turnover costs and a vacant unit? 

It's a townhouse in Ohio, and as per the estimated financials, I could be looking at $400 per month in cashflow.Problem is...

I am a 1099 buyer and a mortgage lender as well.

I'm in South Loop near the Loop, lake, Grant Park, CTA, and a variety of hospitals / schools, so renting out the room on a mid-term basis (32+ days) for a premium was the best strategy for me.

I just used cash to build my first 3 specs no loans at all.. once done and sold then I went to lima got one loan from them.. then went to local bank ( much much cheaper) and got a 3 mil  guidance line and went on to build 30 or so in charleston.. you have to prove the model.. its not like buying a rental where lenders look strongly at your fico  fico is required but not the main consideration like and investor loan and all you need is 20% down or 30% down and a few bucks in reserve that wont fly with spec loans..

It is an area you are likely more familiar with and closer to which could be helpful for your first investment and as @Sarah Kensinger metioned, you may be able to do a MTR.  

BTW, the rental property is cash flow positive.Good questions @Bob DoleJust a quick not to clear up any confusion, Flips are not rentals, and as a result, don't depreciate.

These are professionals with additional training and a stricter code of ethics.

And as more happen, more will happen just out of FOMO. 

Now, over a year and a half later, he sent a certified letter last week demanding the security deposit or legal action within 30 days.Please advise.