Do I have to call an Insurance company with the property address for every individual property every time, to get that estimate? 

Lets not forget the sea of individuals who are making fraudulent claims, collecting tens of thousands of dollars at one time.

What you're paying is fairly market given your experience level.Are those friends working with private, individual lenders as opposed to funds?

You might simply be outbid by individuals who can put down 40% or more.Consider looking at asset classes that aren't in a feeding frenzy right now. 

Even if you like a certain individual, you'll want to talk to others just in case the others have a certain skillset that you need. 

Don’t think so, each property is treated individually. 

I don't know the individual you mentioned for possibly mentoring you, but these are some basics to find out from them before you put your hard earned money into a mentor."

I would go for individual awnings, no need for an entire long covering.

Understand that there are two different kinds of "private" "lenders" ...The first are as you're probably thinking: individuals in the business lending out their own funds on hard-money terms.The second are lesser known / understood: people you already know - friends, family, neighbors, etc. - who would be willing to invest in your deals for a return on their money.

Any suggestions or trustworthy individuals?