Would this lower my insurance cost or make the units look more attractive (essentially would it pay for itself)? 

I work with and know many people who live in the Boston area and invest up in the NH market due to the lower price points, more attractive cash flow, and better landlord/tenant laws.

Ya see, when you are a property management company you are holding hundreds of thousands if not millions of dollars in trust accounts at any given point & time.

@Stephen Witkowski, what I find most often in these Reports is the same as what is on this one: The Buyer is expected to get a 30 year mortgage at a very attractive (owner-occupier?)

This assumes you will have come up with $8.7 million to buy those houses. 

A property of any kind that is in poor condition is a sign that the owner is disinterested, not engaged in the market and possibly willing to get rid of the property if you can come up with an attractive way to eliminate their problems. 

We are willing to push our plan in rental property in Ontario.It would be a great opportunity with the from the group refer a real estate agent, mortgage agent, a lawyer and accountant for start a team and to push on my first venture in real estate.As per my research Toronto is the most populated area in Ontario with 2.7 million followed by Ottawa, Mississauga, Brampton.

That's super attractive. 

From the PM's I've talked to, you generally want to buy in an area where you can attract tenants with income that is 3X the monthly rent (2.5X on the low end).

And there are a million sites online all asking for membership and money.