If so, get a 12 month history of expenses. 

Other areas in north side like Avondale, Logan Sq, Irving park, North center are expensive right now but deals can be found still...You might have better luck looking into Albany park, Portage park, Jefferson park, North park etc...You should look into FHA program with 3.5% down.

You aren't considering all the expenses.

So total income is 1300+200+900=2400 and total expenses are 2700.  

@Stephen StokesYes, where there's a will, there's a way and the way to come in under the seasoning requirement is to use private lenders or non-agency money that will undoubtedly be more expensive in both the short run and long run.  

The area is facing an affordable housing and rental crisis with nothing in the market under $250k on the bedroom community side and a median home price over $900k in Jackson. 

However they have no savings for repairs, capex, vacancy, or management.I think if you can find homes in that price range in a decent neighborhood, basically BRRRR them without the refinance, and sell at a price which yields >10% ROI after accounting for all expenses, I would imagine you could sell it quite quickly.I doubt you would even need to go as far as finding a tenant or management company.  

Just being around the lead based paint won't hurt them.Majority of the houses here were built before 1978 and t's too expensive to de-lead them - some neighborhoods MV is around $50-60K.

Say we have around $100k to put in, we could put 25% down (standard around here for a conventional mortgage on second/investment home) on either 1 $400k home, 2 $200k condos, or 1 less expensive place needing repairs (putting some of our capital against renovation).

I decided to rent my 2 extra rooms to house hack, greatly reducing my expenses.