You can honestly say that you don’t know on the disclosure form, make sure everything is nicely painted with no chipping paint, and you’re pretty good (depending on local regulations).

All of that has to be put into the equation for the true cost of added regulations on the rental industry. 

before pre foreclosures became highly regulated in Oregon and WA that is where we bought most of our deals.. but they had to pencil just like cash.. you cant exit these with any money if you dont buy with equity up front.  

To me if you are mixing different state laws and regulations and processes you are not making a tighter ship but one with more holes to exploit.Remember EACH of those things you create must be managed separately or you just allowed the person who sues you to pierce the veil and they now have access to everything. 

Do they offer any guidance on the tangible property regulations? 

Guidance from the Illinois Department of Financial and Professional Regulation on how HOAs and COAs are supposed to manage complaints/disputes:https://www.illinoisrealtors.org/blog/idfpr-publis...

You are not prepared to invest yet.You are starting a new business and are going in blind with both hands tied behind your back if you have not studied, memorised and fully understand your state landlord tenant regulations.

The new architectural/safety regulations that occurred during the previous ownership can be waived for the old owner but once the property is leased to a new establishment they have to comply to the current regulations.

I have three basic criteria for a property that I'm about to buy:-300K or less-good appreciation predicted-AirBnB revenue is high - a city/place with frequent visitors-Has condos zoned for commercial use or some other category that minimizes the chances of regulations around property usage as an STR.  

Further, if you start delegating tasks on your own properties beyond simple admin (such as showings and signings) and the employee is engaging in brokerage services such a lease negotiations, you are also in licensee territory.Best to pull out the state code and REC regulations for the local guidelines.