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

Starting out, single-family was my go-to—easier to manage and a great intro to the game.

I have a pretty straight forward return with a W-2 and a K-1 from an LLC. 

This deal highlights the power of well-executed renovations and a strong partnership in achieving impressive profits.

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

One of my friend happens to be a RE agent, landlord and a property manager himself and he seems to feel that as long as she pays rent on time and does not create nuisance, not to worry much and just keep do a quarterly property inspection.

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

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.  

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.

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.