4) Most importantly: Do I need to get a RE lawyer to draft a contract?

I have a condo in NYC and my lawyer told methat the condo association can foreclosure on my apartment

Come up with a clever marketing campaign like the Lincoln Lawyer but for Real Estate and Uber. 

I guess it’s a nice little cottage industry for the lawyers too specializing in these types of evictions etc .

Not sure what you mean there.Assembling a winning team consists of finding people you trust to: Identify winning potential properties, negotiate deals, inspect properties, complete accurate bids for rehab, contractors, lawyers, ect.

I did about 3 deals without one (eeek) So I came across online a legal zoom website and thought I should breeze one up for $149 or more or should I sit with a lawyer and have one drawn up?

Once again you obviously are a lawyer and can read between the lines. 

I've read a lot about driving for dollars yet I'm unsure how to do a title search in Ontario without being a lawyer or real estate agent.

I will chalk some of that up to how newbie we are and a little of that also goes into the team - our first lawyer, even though she had investment property of her own, did not seem to understand what was important to us and how to protect our interests or how to finesse dealing with the seller's lawyer.

I would also talk to a lawyer with the $$$ at play it could be worth his time.