He's finding more properties than I can get qualified to purchase.If you're looking for commercial (5+ units) @Nathan Holsather is a good bet as well.If you're looking for someone who does value-add residential, @Jordan Moorhead is both a rehabber and an agent.

Especially when the city charges us thousands of dollars for permits and inspections.

They charge a loan renewal fee in the $400 range.

The seconds reason is that the purchase is made without agent that usually charge 7% percent and this money is save to the seller. 

Would a HML be my best bet on this property .......... as i may have a better chance for being approved to do most of the repairs , as well as Having the best chance of getting a loan for the property?

The conventional may be my best bet, but I do have my house that I can work with.

Your best bet is to have your agent contact the listing broker's employing broker and let them know the situation and request to be present when your offer is presented. 

The major downside in my opinion is that if you paid $80K for the NPL and the home has a value of $150K, you will be charged by OSC for the $150K coverage. 

For Probate direct mailers should I be targeting the person who is put in charge of the estate?

Also providing basics like coffee, tea and water really help with perceived value thus you can charge a little extra as not all places offer that.