Most do $1mil in value (not necessarily equity) per LLC as a rule of thumb.Whether to do 1-to-1 will depend on how much flipping you do and your personal preference. 

I prefer to try to avoid locations on those list, and focus on other areas with strong appreciation, so I can have appreciation, positive cash flow, and not be quite as frustrated during the process.

Ironically, I would walk away with what I put in - $150k.I would like to buy a SFH or preferably a duplex where the monthly cash flow could be about $150 - $200.

I'm a bit more introverted and prefer not to go out of my way to talk to neighbors.

I was more concerned of overpaying for a property that would have higher chances of being vacant because of 3 beds being preferred and also having less appreciation over time.

I prefer someone with experience in Screening  tenants.

I think my preference now might go to the renovated/younger small multi to start with.

We prefer longer term debt so you aren't forced into a decision by the market. 

I have my primary residence loan through BMO but have heard that going through smaller lenders is sometimes more flexible and preferred by real estate investors.While I'm at it, any good insurance agents to shop rental investment rates with?

Short answer, find a contractor that you trust and have preferably worked with before.