A good friend of mine recently managed to pick up a modest duplex outside Phoenix that looked risky at first glance.. low rents, older neighborhood.. but with a few smart upgrades, it became a steady earner in under a year.You mentioned your worries about remote investing and the challenges of managing properties from afar.

I have three vacancies in a C class neighborhood and the only people I’ll rent to now are Section 8 with a small tenant portion.  

Sounds like you are better off in a high yield savings account like @Dominic Mazzarella mentioned...Just out of curiosity, Nilusha, what Chicago neighborhood are your 2 flats in?

He did mention that if the lot is facing a major road, they board would consider rezoning to MF, but since my lot is about 7 spaces into the neighborhood, it probably wouldn't be approved.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Signed into law in 2021, SB 9 is designed to address the housing crisis by allowing greater density in residential neighborhoods.

It is never good to be the biggest or most expensive house in a neighborhood.

That's great to hear that you're graduating and you want to get into multifamily.I would start off in a commercial real estate firm, learn the systems, the sales/buying process, how to analyze deals etc...

If you start buying properties in Class C neighborhoods, you can take advantage of higher and more stable rents/renters with Section 8 vouchers. 

Fortunately, I was thinning my herd back in I think 2014 or so by getting rid of a few (experimental) investments in cheaper neighborhoods.