(yeah, maybe I shouldn't be broadcasting my sick twisted forms of entertainment and strategy should I)BUT, most importantly is KNOW YOUR MAO and follow the math. 

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

This growth seems a bit slow for me, and it might not be best for selling.

Risk comes in many forms and is hard to quantify. 

Be friendly :), it's always good to form relationships with the city. 

Shoot me a DM - I'm happy to chat, although BP is kind of wonky for me, especially on mobile. 

For context, the two extra parcels form a triangle with my subject property.

I think for someone local to the area it would be significantly easier to find good deals that it was for me.

And yes, attorneys make money from forming LLCs, but they make way more when you were negligent and didn’t know what you didn’t know and end up in a lawsuit.