Hey Ryan, welcome to BP and the wonderful world of real-estate investing! It's nice to see new people enter the Winnipeg community, and so young!
Also, you want to make 1 million in 5 years? Definitely possible with the right people supporting you and with a strong ambition and "why"
I'm going to be taking action just like you in a couple of weeks, so I can't really help you with real world experience or a realtor. However, I can point you towards people who do.
Go to meetup.com, and sign up for Truly Invested, Team-made real-estate, and MREIA. Truly invested is having their meeting this Thursday and Team-made is having theirs I think next Monday, so sign up before it passes by.
As for backgrounds...
Team-made real-estate: every event is free, offers a incredible coaching program, great people and atmosphere, focuses on relationships. Great place to start for newcomers.
Truly invested: First event is free, after that is $45 per month. Reminds me of BP, about how they don't try to sell you anything at all, and it's just a great, comfortable place to network, connect, form relationships, deals and partnerships.
MREIA: First event is free, after that I think it's over $55 per month now, it increases over time. This group is Stefan Aarnio's group. He's a millionaire REI, winner of many REI awards and Rich dad hall of fame, he's a really big fish in the community. Offers coaching, but the good coaching requires you to be a experienced investor already and have lots of cash for the expensive, higher level coaching. A "get-sh!%-done" attitude and a serious atmosphere.
See you at the upcoming meetings!