Do you think successful RE entrepreneurs need to chase small time investors money, mentor newbies and write books about their winning strategies in an already over competitive / saturated market?

I am looking at the same strategy.

And if so would I be able to do a Cashout refinance like people do with the BRRRR Strategy? 

It's been a year, and contrary to my initial profit projections, I've been consistently losing money.

You might have some luck with a house like that in midterm rentals but you'd have to be willing to really work on your strategy.

Property prices are very low relative to Ontario and am curious if this would be a good first entry level market to invest in with the hopes of high cash-flow and a long term hold strategy.

The first thing I'd recommend is determining what your goals/strategy are-- looks like cash flow based on price to rent ratios in these areas.The reason I'm saying this is because rentals or managing properties in general out of state present additional challenges, so you have to understand that going in and know that things will come up. 

What is the best strategy to use in Orlando when first starting out?

I flipped the script and just started working with wholesalers who consistently send me deals to fix and flip.

Got it, that makes sense.I would say hone in on what rental strategy you want (STR/MTR/LTR).