There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

I'm not sure what the issue is on this.

Exterior attachments like decks and stairs are always HOA issues so I can't fathom how the driveway is not.

As lenders, well issue a prequal/preapproval letter if we've analyzed your income, assets (bank and brokerage statements to establish that you have the liquidity to afford the down payment, closing costs, and reserves), review credit of the guarantors, review the relevant experience to ensure that we're not throwing our money away on newbies that are wandering around in the dark, and have put together a reasonable plan of attack for the project.

@Francisco Ruiz ensure that if you are obtaining financing, you ask/ensure with your lender that they do not have any issues with the fact that the property you are acquiring may appraise as "rural."

If I wanted to transition it to an LTR in the future, my best guess is that I could probably find a tenant for around $1,700-1,800/month without too much issue. 

Satanic, my foot.This just looks like the result of run-of-the-mill substance abuse and mental illness issues.

Sewer issues in Chicago are very common which is why I ALWAYS recommend / almost require my clients to get them done + if there's trees in front or in the back of a property, there will almost always be plumbing issues + needed rodding. 

If you didn't do any testing, you are definitely going to have an issue if the house was covered in mold.

Should there be any issues with your property though, that is one of the first things you could expect2.