@Jonathan Klemm thanks for the mention@Ali Farhat Jonathan is correct that you may still have some opportunity depending on the Zoning designation for the lot, and how many existing units are Legally Recognized by the City.You can Check the Zoning Designation here on the Chicago Zoning MapFrom there, you need to check the requirements for your lot based on the Chicago Zoning Ordinance (Note: RS-3 does not mean 3 Units.

Buying a Bed and Breakfast with potential for events and short-term rentals (STRs) can be a fantastic investment, but as you mentioned, with the market saturation and seasonal challenges, it's important to run the numbers carefully.

Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

Pros and cons have been mentioned already and I agree with them - as an investor who owns Section 8 properties.

@Skyler Shively, as mentioned, it is a tough niche to find a lender for. 

The inability to scope the sewer line is concerning, as you mentioned, there could be blockages or other issues that need attention.

Like @Carlos Valencia mentioned, its good to consult with your lender to see what else is needed prior to reaching clear to close or CTC on your file.

Any others that you guys use that are worth mentioning ?

I also love learning, so if anyone has any resources they'd like to list, link or just mention - I'd love to hear about them. 

In addition to accepting $40K less than ask, I forgot to mention that I already gave the buyer $5K toward cc.SOL on backups at this time even though we left it on the MLS to show while under contract. 48 DOM.