So if it is leased through spring 2025 you need to provide an executed lease termination agreement. 

Owners are supposed to certify to the Board if no sales were generated in any particular month, as well as provide a copy of any Colorado sales tax return or alternatively, a report from AirBnB or VRBO regarding the sales for that month.I find this invasive, crappy, and a whole lot more that shouldn't be said in polite company. 

Negotiating a security deposit amount is not a red flag for me, especially with over $10K in estimated moving expenses (professional movers) and move-in costs (1st month and security).

Make sure the buy out agreement is worded properly though so it is not a prepayment of rent that will be due in the future.You must refund the security deposit or provide an accounting of sums deducted from it, within 60 days of lease termination.

The STR doesn't provide access to rest of house as common area so they have their privacy mostly.I'm sure you can creative with extra rooms, a garage turned living space, ADU, a furnished basement, etc.Good luck!

They stated due to regulatory changes in IL, they can no longer provide those reports for rental applications.Does this mean I no longer can do a background check in IL or is there a work around with possibly another service I can use?

As you're already replacing the old tile floors with LVP, installing new toilets like the American Standard Cadet 3 during this process is practical and will provide a more modern and efficient bathroom setup.

Any other insight that you can provide would be greatly appreciated.

Partnering with Glenn Klingensmith provided valuable local insights, making this an attractive and strategic investment.

There are some interior designers who provide these services, but you may have to search a bit to find what you are looking for.