For example, I used to live in Berkeley, CA, where it is extremely difficult to evict tenants, even when the owners want to move back to the unit, sometimes the city would ask the owner to find other homes if tenants have been living there for some time.

Anybody from a major city that only has cash that can’t be verified in any way would immediately tell me they are a drug dealer or stripper or worse

Then a “guru”  that’s on yotube that’s in my city  said he’s licensed so when I looked him up, I found out his license is suspended and he has an open complaint against him.

Baldwin county alone has four cities in the top 10 for fastest in growth in the state.

San Diego is a great city!

If water came up through the drains, complain to the City of Chicago about poor/malfunctioning  sewers.If water came in due to collapsed/clogged drain pipes.

@Jim Adrian it’s a complete guy, sans most of the flooring, because the place has been vacant for 10 years, the plaster ceiling is falling down everywhere, walls need to be reconfigured to make it fit a SFH instead of a Duplex better, Mechanicals all need replacing due to rodent/critter damage, and city code will require electrical service upgrade and new water service, etc… It’ll be a fun project, has good bones, just the soft meaty stuff inside that sucks.

I primarily/ultimately want to get into multi-family complexes and am unsure as to whether I should aim for some (section 8) SFH in Baltimore City to build up my capital/equity.

I also understand that it might be a case of the city simply saying "no," and 'Id have to consider a plan B.If anyone has a contractor to recommend, or is a contractor themselves, I'm all ears. 

At $18k NOI, you're buying a 4.5 cap which is WELL below the CBRE cap rates for stabilized C class properties in most all cities.