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

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. 

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.

I find trying to slog my way through government regulations to be a bit overwhelming.

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.

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

Ramsha - most of the regulation for a STR is controlled by the neighborhood HOA.

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.

The final wild card is government regulation and how it could affect the investment.