For these reasons i am confident you do not need an account per unit as having that requirement would be crazy complicated (the opposite if kiss).in addition, how will anyone know that you are not following the law?  

Yeap, exactly same as Zillow's Zestimate increased the price of houses.

Just make sure you are saving towards those slow months during the peak months, buy a deal at the right price (don't overpay just because its a turnkey STR or you think it will make more money than projected), and look into ways to increase bookings during those slow months with some marketing and operation tweaks. 

Also, as long as the house appraises, taking broker commission and using it against down payment and closing costs means lower cash requirements for me which increases my CoC returns.

Now that you know this little secret (that most don’t), you can make informed decisions when it comes to increasing rents for new leases and renewals.

However, on the renting side, we have seen an increase in inventory of days on market too. 

The lawyer says he is pretty confident but since he has not read the entire lease, he says he can review it at additional cost if needed.

I focused on adding modern luxury amenities to increase the property’s appeal to the high-end market.

Many of these areas also benefit from both rising home values and increasing rents.Ultimately, successful investing comes down to selecting a growing market, a strong neighborhood, and building a reliable team to support you.

If Oak Park allows STRs, leveraging that history could make the property stand out.That said, unless the home has been preserved as a landmark or has unique historical features, the value boost may be more about novelty than a significant price increase.