My whole goal with real estate and increasing my financial education is to free up my time where I am not doing the things I hate so I can do the things I love! 

I'd recommend starting off with more education.

Mainly because that was what was financially and educationally available to us at that time. 

If it can mitigate your cost of living over the next few years, will cash flow when you move out, and there's not extreme volatility of the industry there (just a steady slow down) - I think it is worth purchasing. 2-4 unit owner occupied's are the best cash on cash in the game and a great starter education into real estate investing.

Money management is not a skill that's taught or honed in most educational institutions.

I don't but in an effort to educate myself I have said "yes" several times and answered their basic questions.

(I found these people on FB groups, Connected Investors, Craigslist) I don't want to pay some guru to get leads or education.

Feel free to DM me if you want more specific advice.Good luck and get educated!

I've been spending sometime now educating myself and looking at a few markets, and I'm narrowing down to either Indianapolis-IN or Columbus-OH.

I would focus on educating yourself on everything Canadian Real Estate related.