Foremost will allow you to add as many as you want to one policy, although I don't know of a major price break or discount that isn't simply just the multi-policy discount. 

I used Zillow a lot when I first started looking for property to buy, but I ran into so many problems that I now use Realtor.com almost exclusively.

If I let the foreclosure process start to take place, and have the borrower (my grandmother) willing to work with me, would it be possible for me to purchase these notes before foreclosure at the usual discounts?

It's uninsured so it only has a 5 day exclusive bid period for owner occupants and no investors.

I have exclusively purchased condos/TH and that is just because there were more deals to be had in those days in that category.  

The lender won't accept a discounted payoff if the property has equity.If the property is worth $170K or more, then the seller will need to sell for $170K or bring cash to closing for the difference.

You don't need a lawyer for small claims, document everything you can and get a judgement...ask for the max, don't discount anything. $3400 sounds low for all that.

Perhaps give away (or steeply discount) a few lists to get some positive feedback first?

Even at a substantial discount the property tax would eat you alive and result in negative cash flow.

I'm sure your tenant would LIKE to have that convenience but sounds like too much of a hassle, cost + maintenance on top of that for it to be as viable as it appears.You could always tell the tenant that if she renews the lease at $550mo (which was what you were going to re-rent at anyway), and pays on time, she will receive a $25 discount that month to apply toward laundry expenses.