I know of other situations where the pump had to be upgraded but that cost was minimal to cost of heating. 

What matters most is how WELL your policy is designed so that you can minimize the length of time it takes to catch up to and surpass where you would have been had you simply taken your money and invested directly into whatever you were planning to do.

That balcony may be cantilevered, and the braces only there to minimize some of the bounciness that you feel with cantilevered balconies.

I would say managing the construction of a 3500 sqft house through demo of an existing structure, new site work, at carrying the project all the way through to the end would be quite an undertaking - especially with minimal construction experience. 

But I would definitely find out how you can minimize the amount of taxes you’ll end up paying if you liquidate if any.Feel free to reach out if you want to pick my brain about Chicago in general and I can recommend an investor friendly realtor.

Vacation homes can make money during a pandemic (Or similar) if the travel costs to the destination are minimal.

@Bernard Reisz would probably suggest you learn about checkbook control IRAs to minimize your transaction costs.

I don't generally recommend using retirement funds or all your savingsSet your expectations realistically House Hacking and Flipping are good options but if we all could make $120,000.00 a year with minimal funds or effort we all would. 

Even if it was all above the table with your SO, you would want to consider your 121 exclusion - that could be worth MUCH more than the minimal losses it may create.

Besides obviously screening great tenants, do you offer some sort of “bonus” if the wear and tear is minimal and it is move in ready for the next occupant.