I'm still VERY new to everything and this would be my first rental property/househack.I have found a property of interest, it's a duplex, one side is 3BR/2B and the other is 1BR/1B - They are on month-to-month lease... is it still possible to obtain an FHA loan and easily get the tenant in the smaller unit to vacate when their monthly lease is up? 

No big, national, publicly traded banks will do this loan type.

Unless there was a lien recorded in the public records I doubt the insurer will accept liability for the matter. 

Obtaining permit inspection from the city of Chicago is never predictable and your GC is not going to be able to predict the outcome any better.  

You can obtain a Jurisdictional Determination from the local Army Corps office.

How will you handle the flow of the money and what will be the "face" of the entity/entities to the public (tenants, vendors, local and state government).

However, they shouldn't be able to just arbitrarily increase your purchase price without your agreement (unless you are at the point prior to having the public report. 

The tough part is finding the folks in forbearance since this isn't public info.

A SSN is required to obtain an EIN, but that doesn't necessarily mean the child LLC income would pass directly to you.

It's not my business model, but having anyone live outdoors like an animal in the USA when they hand out Section-8 to illegals upon arrival is a hard pill to swallow.They need to sort the homeless into short term vs. forever types.Steer the help to the short-term helpable when they need it, and publicly house the "more eccentric" types out in the county away from civilization.Maybe have a poor farm where they can plant gardens to feed themselves if they are able...something to keep them busy.It would give all of them someplace to live indoors at least.This street begging/tents on sidewalks thing is Un-American.Just my 2 cents