Get educated and comfortable with the process of RE investing and ask plenty of questions. 

I'm not sure how it all works, I'm trying to get educated so I know what to  expect ( and not look like an idiot) when talking to a  hard money lender?  

Not enough education from the right people. 

You just have to decide whether your market is a flip or cash flow market, get some education, find some funding, and get to work!

I'm new to Bigger Pockets and am interested in becoming educated about buy and hold rental properties.  

Best/first thing to do is get educated.

@Brent Coombs - Thanks for the perspective - I am certainly curious as to where this owner went wrong...Ryan Goldfarb - thanks for the insider info, and the rent control info - Definitely something I need to educate myself on.

Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookCouple good reads 9 Reasons You Couldn't Find A Buyer For Your Wholesale Deal Don't Start Wholesaling Until You Read This: Wholesale Advice from a Fix and Flipper How to Start Wholesaling: Getting Past The Education and Into the FieldUltimate Guide to wholesalinghttps://www.biggerpockets.com/renewsblog/2015/01/31/ultimate-beginners-guide-real-estate-wholesaling-2/Download BP’s newest book here some good due diligence in Chapter 10.

I would invest the upfront effort in self-education (there are a variety of books which will provide you a good primer on real estate in Canada and you have already found one of the more useful sites on the Internet).Once you know which area(s) of real estate investing are of interest to you, look for a local real estate investors association or meeting in Winnipeg and attend an event or two.  

I would recommend educating yourself on that before going that direction.