I’d be happy to connect and share ideas on building a solid plan, like assembling your CORE 4 (agent, lender, property manager, contractor) to help streamline your journey.

Don't let them choose for you.Just inspect what you expect....Also I would talk to housing office in Memphis to get a feel of how many people are on the Section 8 waitlist, what kind of rents they pay, what zip codes are they targeting, see if they have any stats about how long tenants stay and average rent.While a lot of people try to look at google street view to get an idea of the neighborhood, there is no substitute for visiting in person.

Networking with Canadians who’ve invested in the U.S. sounds like a great idea.

I think all of your suggestions are great possible ideas to do this deal! 

3: I have no idea how to determine how much to borrow verses pay cash?

Hi Ethan, I would not entertain the idea of getting more money from this tenant in order to potentially increase your cash flow. 

Would it be a good idea to get a real estate license and work in real estate or are there other options to get in Missouri to get real estate experience without a license? 

I don't think you're being too ambitious, I think its a very smart Idea especially in Chicago where there are an abundance of 2-4 unit buildings!

I'm curious about number 4-could you expand on the idea there?

Also, good idea not to put it out there on the internet that you have that kind of equity, that will just attract more scammers!