Lack of supply is mostly purposely created by outdated zoning restrictions, paranoid nimbys, inflation, and our economic system in general. 

Dont like the cut-throatness and nastiness within some offices of some of the big "boiler room" firms and some of the restrictions on territories and property types, but cant afford to sacrifice actual success if thats the type of place you gotta go through, at least at this point in life...  

I would really like to continue to invest, although with the interest rates, the restrictions and prices in Canada it is a challenge. 

Additionally, there is NO verbiage that states the Landlord cannot impose verbiage in a Lease of a non-pet owner to prevent future pet ownership...

are there any restrictions on number of rentals?  

Illinois prevents imposing late fees until the rent is 5 days past due.

However, be cautious about the LOC's terms regarding real estate investment use and potential restrictions on refinancing.

First you would need to check and see if the area isn't restricted for STR, and the market is there to support a STR.

Consider both county and city restrictions that may affect certain neighborhoods.

Right now there are no STR restrictions unless you are in an HOA.