I was with them for 3 years, and during that time got 0 money on my investment, and the communication was not great. 

I signed a 12 month lease to start on 2/20.

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

Then focus on finding professional vendors that can clean/repair, as necessary.

Just stay conservative on ARV and rehab budgets, and you’ll be off to a strong start.

With a duplex you get more control, maybe more write offs, but obviously more hands on and the potential for higher vacancy.

Definitely  cant put a price on learning experiences.

We received a notice from the HOA and waiting on a voting date & time on the proposed changes. 

I have an STR and previously did not allow pets on our property out of fear that they would destroy it. 

I see a lot of syndication deals where you follow the money (I have not reviewed the above so I cannot comment on them) where the money all goes to the sponsor in upfront fees and other entities and all the risk falls on the investor.