Our question is can this be done tax-free?

This article that outlines the Cannabis Regulation and Tax Act explains, "The Act applies the restrictions of the Smoke Free Illinois Act on smoking cannabis, and provides that property owners may prohibit the use of cannabis by any guest, lessee, customer or visitor.

Marketing, payroll, and real estate taxes just to name a few.3.

Tax write offs?

The legal description is in the property deed and the property taxes roll. 

Excerpt from our rental criteria:RESIDENCE/RENTAL HISTORY1.We will examine the most recent five years of residence history and all legal history.2.Home ownership will be verified through the tax assessors office and/or credit report.3.Rental history will be verified through the property owner and/or rental agent. 4.Rental history reflecting any unpaid past due rent, damages or fees will result in denial.5.Rental history showing excessive property damage, excessive noise, or unruly behavior will result in denial.6.Three or more notices for failure to pay rent and/or to comply with the terms of the rental agreement, within a 12 month period, will result in denial.7.A person with an eviction or unlawful detainer on their record may be approved if full restitution has been made.

It doesn't count as an expense on the tax return. 

They remit the taxes.

Plus numerous tax advantages.

Now that I have the time, I'd like to organize my portfolio to maximize legal protection, minimize taxes, position for growth, and not leave a headache for my family.