Once you hit a certain number of loans (check with your state dept of banking and finance or dept of business regulation), they might require you to have a license.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

Now, you can get some wholesalers but they usually don't know if the property will fit the requirements and regulations but you can learn that from the Realtor. 

I'm not familiar with Canadian regulations but you should look into how you can get access to money if you don't have any.

As more people placed more properties in STR inventory, and as more municipalities taxed and regulated the industry, the profitability of the overall industry has reverted to a much more aligned (lower) risk adjusted return.  

The first thing here would be the regulations and laws governing acquiring properties, managing properties and selling properties.

You also need to consider any STR regulations.

Ensure that you thoroughly review your state regulations and display the necessary notices before changing any locks or removing any items left behind.

If you are able to manage it yourself, I think you will get a lot of very helpful education in real estate by spending a least a year or two doing that.You'll be able to work with property managers a lot better if you've done the work yourself for a bit, and it also helps to get familiar with the various laws and regulations you have to comply with as the owner, even if you do have a property manager in place (e.g., the new RI rental registry and associated lead paint inspections/certificates).It's up to you whether you're able to do it, but I think you'll get a lot out of the experience if you can try it for a year or two.

Always research local regulations before investing.The Importance of a Local Investment TeamA knowledgeable local team is essential for success.