As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

Programs that market themselves as shortcuts often cannot replace the depth of understanding that comes from study, experience, and engagement with the legal framework surrounding real estate.Consider taking time to familiarize yourself with local laws and regulations.

Being from illinois, I do get a kick at how much regulation goes on out there in tennessee - where people give me guff about how our local politicians here are so intrusive. 

If you hired an agent or a broker to work with you, you'd be covered - but regulations & laws vary from place to place.Screening is best done by establishing a set of guidelines to qualify applicant tenants, then sticking to those rules to avoid legal issues (and for your own sanity).

SPECIAL RULES FOR SECTION 1031 LIKE-KIND EXCHANGE TRANSACTIONS, page 135 states:". 01 Taxpayers are provided the relief described in this section if an IRS News Release or other guidance provides relief for acts listed in this revenue procedure (unless the news release or other guidance specifies otherwise)..02(1) The last day of a 45-day identification period set forth in § 1.1031(k)-1(b)(2)(i) of the Income Tax Regulations, the last day of a 180-day exchange period set forth in § 1.1031(k)-1(b)(2)(ii), and the last day of a period set forth in section 4.02(3) through (6) of Rev.

My CIty does not have a boarding house regulations or restrictions which is one of the reasons i jumped on this.

As Bernard pointed out, the language of Regulations makes this stay count BOTH for 2024 and for 2025.

She knows all of the regulations for the area.

The STR regulations are very black and white and I don’t see many, if any, clients having issues with obtaining insurance if the house is in good condition.

Not following the requirements (within Seattle city limits will likely have additional rules and regulations) opens the seller up to liability.Additionally, the seller always has the option of offering "cash for keys" arrangement but be sure that no funds change hands until after the property is vacated and locks are changed.John