I have looked at the ADU rules for Escondido and San Diego city as well as what CA mandates in the CA ADU regulations (which puts a limit on how restrictive any city can be with their ADU rules).So with your financing and plan to add an ADU, it would not be a smart decision to pay extra for a zoning that you would not be able to fully leverage. 

Also note that the cities of Portland and South Portland (and other surrounding towns) are taking a hard look at short term rentals, and additional fees/regulations seem likely.

Local rules & regulations.

If you're strictly looking at the MLS offerings  I would strongly suggest networking and reaching out to the many Chicago wholesalers on BP so you can expand your search with off-market deals.  

Our bank has very strict terms and one of the lines say that we need to sign off on everything that is different and a change order must be submitted with both of our signatures on it.

(Some rules and regulations)-Did you know you can purchase a property with a self-directed Roth IRA?

Licensing laws are strict and the DOL powerful.

The different cities all have different regulations on short term rentals.

However, I do not know the regulations their in Canada. 

I wanted to share this article...IR-2018-206, October 19, 2018WASHINGTON —The Treasury Department and the Internal Revenue Service today issued proposed regulations and other published guidance for the new Opportunity Zone tax incentive.Opportunity Zones, created by the 2017 Tax Cuts and Jobs Act, were designed to spur investment in distressed communities throughout the country through tax benefits.