Keep emotions out of it as much as possible (easier said than done, I know).If you feel uncomfortable saying you are not the owner (when in fact you are) consider putting your properties in an entity, ie; corporation, LLC, trust, etc. 

If you do decide to rent to them, which again I would not recommend, give them a month to month lease so that it will be easier to get rid of them if things go bad.

Generally your target monthly rent should be a minimum 1% of the total value of the property.

I've thought of just sending a handwritten letter as well but I'm too impatient for that since it's one property rather then targeting a group of properties.

The target property is a nn-warrantable condo.

I know it was a pain the first time, but after the first one, they get significantly easier. 

I need to target Intel populated areas.

Way easier and cheaper.

Although, I have turned the property I am currently living in (I own) into a duplex which would allow me to rent and move out into another to have as primary residence. will this make things easier?

I'm ready to invest another $50k or so and was considering investing out of state, small multifamilies in less desirable areas near me, or to continue investing in my comfort area.About the target property: I would classify it as an A or A- area based on what a lot of people call B and C areas around Chicago.