Since we are both in Chicago, I would highly advise checking into the landlording laws here. 

Please note that I have 25 years of experience renting out apartments and houses in three other states, but I’ve never done so in MA, so I don’t have experience with local MA laws or vendor expenses. 

I’d argue that a mix of custom and arcane, broker-serving laws sustains current practice, not market demand like for Delta tickets or Colgate toothpaste.

been there done that its how I used to do pre foreclosures out west before the laws changed..

Quote from @Mike Arias: Quote from @Chizitem Ibeneme: I'm a college student, and I plan to start investing in multifamily homes once I graduate, and I recently started looking at deals on Zillow just so i can practice underwriting.

Oh, and the platforms are actually more friendly to the buyers than sellers. that is why they will take money from hosts on practically any complaint from a guest, or suspend a persons listing until they can prove/disprove any guest allegation.

As a CPA and real estate investor who is a general partner in two syndications, I want to share some practical advice to set realistic expectations.

Next year, your income may change; your family or tax situation may change; tax laws may change.

I feel like having some good experts helping me clearly identify best practices and targets for success (instead of guessing) to be extremely helpful. 

Check the states laws- depending on the strategy, you may not have to register.