We have consulted with our accountant and got all the scoop on what needs to be done.

There is no need for this.

Or do I need a specific software to obtain this info? 

Recognizing the potential in properties with minimal improvement needs allowed us to streamline this process.

If you are with a cloud brokerage like eXp or Real, you can just move and stay under their umbrella with a new state broker after you complete whatever Illinois needs for reciprocity.If they don't have a TC team, you will need to complete and upload all of the paperwork, but they should have compliance videos for you to do.

Other option is giving a small portion of equity and splitting profits and ongoing costs evenly, but not sure how much equity to give or how to logistically buy their equity out later on if I want to keep the STR for life.

Currently a majority of the existing mixed use buildings have the commercial space shuttered with the owners just biding their time until the real estate prices make sense for them to rent out or sell - or they are just asking way too much in rents for any businesses to survive for very long.

Can  you  add the extra cleaning fees to the extended stay, vs the guest would need to make a new booking to include this service?

Let me know if you need anything.

A lot of times when you make a bedroom out of a room, but your square footage is the same, you don't end up adding much to the home.