I spent several months on reading up the stuff and filling out all the forms and constantly pestering my tenant to follow through with her application.  

Tokenization of real estate assets can take numerous forms, but what you’re proposing is to separate the real estate “bundle of rights”, have the property owner sell one or more “rights” but not all of those rights, and represent the ownership of the rights that have been sold by tokenization utilizing block chain technology rather than the county “filing” systems currently in use.  

(They also assured me I would not take the algo hit.)I no longer default to pre-approval as for me, it's bad for business. 

I've read mixed reviews on host experiences with VRBO and Booking.com, so I've been hesistant to list there.Currently, using PriceLabs and tweaking/ analyzing pricing a few times a week.Honestly, my photos are not the greatest yet, but it is a high priority for me to get professional photos soon.

(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. 

That has worked best for me, but it's always best to test to see what results you get.

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. 

Risk comes in many forms and is hard to quantify. 

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