When you sell, Uncle Sam wants his cut.

And, cutting off liquidation options. 

Hey James,Ah, I see where you're coming from—given the Chicago winter, cutting off electric isn’t really an option without risking serious damage like frozen pipes.

Cut expenses and work, no way around it.

IF, they are supposed to cut the power when there’s a fire then they have to buy a bunch of Tesla’s mega pack batteries to power the water pumps.

I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

Those things won't matter if your business crushes it. i feel like it would matter when those things add up and start tearing at ur profit If banking fees cut into your profit, your profit isn't big enough.

They also know when to cut bait.  

The foundation was already approved, permitted and finaled years ago for a 3400 sf house, and its solid and I won't be building directly on the overhang edge; but rather back away from the edge a few feet to prevent any load issues all the weight will be on the longer sides of the existing footing.

@Jason Wray Thank you very much for this response ..I’ve never sold one of my rentals before feels like I’m cutting off a leg and paying close to 100k for cap gains is really starting to eat at me 😵‍💫Any chance you would be so kind as to send me a link to something in the ballpark of what you’re suggesting this way I can get an idea of area and what this type of property could look like!