As such your underwriting should treat this as a duplex.I suspect eventually virtually all of Chicago will allow additional units but it could quite a few years.  

They charge an annual fee, but there are no additional transaction fees. 

Then add 10-20k for additional unexpected budgeting. 

I'll be out an additional 17K/yr until the escrow catches up. 

You still need to do inspections etc. and you are just paying an additional fee.

Additionally, we are open to exploring opportunities in other areas as well.We are particularly interested in:- Learning how to analyze these properties for cash flow potential- Understanding the local market dynamics and trends- Networking with experienced investors who can offer advice and mentorshipWe believe that with the right guidance and connections, we can make informed decisions that will set us on the path to financial independence.

I am going for a house hack with Fannie & Freddie conventional , After my 4th offer was rejected going over listing I asked the listing agent for some additional info and they stated that for this property there were 42 showings within 4 days. 1 cash offer, 1 commercial, 15 conventional and one FHA with 9 waived inspections, 11 escalation clauses and 5 appraisal gaps.

As an example, what do you expect a tenant credit score to be?

Does it show you the complete credit report, or just a score? 

You keep a fractional reserve, plus credit reserves, plus liquid assets, and the rest of the capital goes into the real estate deals that really drive the return for you.