I would consider selling, i’m not necessarily saying you should, BUT only hold if you have a very strong belief in the appreciation of this property. 

Best of luck on your journey!

Single family has more stabilized as there is not enough people who can afford homes.The purchaser is two very distinct types of groups who buy MF vs. single family and single family is bought to own and occupy, MF is bought to generate money.

Very nice!!

I worked at hospital diagonally across street so very convenient and at the time this 2bed 1bath was all I needed.

Very true.

Could happen but very rare. #4 See everything you plan to buy in person. 

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

While I do maintain a relatively modest percentage of my assets in money market instruments, corporate debt funds, and high dividend stocks, I remain most comfortable with the investments I specialize in and know best.  

You'll quickly learn how to manage investments well, which property types and neighborhoods work best, and more.