He can minimize his capital gains if he spreads the payments out over a number of years (plus he'll collect the interest on holding the note).  

Usually with minimal work, vacancies and expenses can be reduced.

Pool maintenance is minimal...definitely upside.  

This property needed minimal amount of work considering the age.

For flippers, this risk is minimal, since their investment is short-term.In conclusion: Firstly, transfer taxes can be difficult to navigate but don’t be distracted by its noise.

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.