The next deals came much easier as my confidence grew. 

Both permits often have restrictions on the industry the holder cannot engage in.- The holder of a work permit does effectively become a tax resident as far as the CRA (Canadian Revenue Agency) is concerned at which point they will qualify for certain things such as purchase a house without being considered as the foreign buyer; hence, foreign ban hammer not weighing on them.

Would love to connect with other RE investors that can guide me/us and build confidence along the way.   

I learned a lot, feel more confident and am pleased with the outcome. 

Once you’ve built some confidence and systems, you can start exploring additional markets.I personally focus on 2 markets that are about 20 mile radius.Make sure the market(s) you choose align with your investing goals, whether that’s cash flow, appreciation, or both.

I was more focused on building the portfolio, and it paid off, as I scaled to 50+ rental units in 5 years.I started my own PM when I moved to a different market because I wasn't confident I could find one as good as my previous manager.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

As an investor looking to purchase an STR in a ski town, I’m not sure I’d feel that confident in a court deciding in my favor, personally.

I met this real estate agent on facebook, seems very active within the real estate community in that particular area based on the posts she's engaged with. 

Since they are responsible for maintaining the relationship with you after the transaction closes, this approach adds an extra layer of confidence and security to your investment.