(Particularly with expertise in depreciation estimation)...Anything helps!

When screening properties, what is the quickest way to estimate PMI for low downpayment (5-10%)? 

- If you were looking for help in the local market, which people would you reach out to to help build an estimate?

Better chance you don’t buy junk that just looks good on paper

Andrew, how much do you estimate it would take you to send out 1000 letters like you described?

The two who gave estimates, I haven’t heard back from again when I told them I’d like to have it done.

The chance of showing the exact same house in the same town to more than one of a few current clients isn't going to be very likely.

Does the property really ever have a chance in my lifetime of going back up in value to $360,000 or higher?

I am not saying this is the only way to do it or you should only do it my way, but there is a better chance of protecting personal assets with the separate bank account and no commingling. 

If I remember right it does cost them something, even to just run a quick automated search.Unless they know you, you've brought them plenty of business, and they think you have a reasonable chance of selling the probably you plan to buy.One alternative is to take a class on how to run title searches yourself.https://www.timios.com/ has been known to be investor friendly.