I think I understand what it will take to make this happen and I'm planning to work with either ListSource or Yellow Letters to get my initial DM campaign kicked off.

What are some good questions to ask on the initial chat? 

I recommend you talk to an eviction attorney to verify.  

If tenant(s) vacate the property without informing the Housing Authority and payments continue the owner, Section 8 may initiate a recoupment of rental payments made for the months the property was not occupied.I feel that if done properly, it is a good investment.

If you're planning to rent it out and not move in until at least June 2020, pretty sure you're stuck with the investment loan initially. 

When I initially challenged that fee, Lender did say that he may be able to lower it but  first would need all the paperwork done, credit pulled, etc. 

You need to verify there are no licenses required to hard money lend.

Some brokers actually have somewhat legit pro formas, with just a little biased tweaking, but you still want to verify those.Something that I've noticed lately, is that some properties that are over 4-units, which should be trading as commercial properties and valued based off of cap rates, are trading more like single-family homes and are valued based on comps and emotion.  

Memphis Invest may charge more initially but they look like they're here to stay and I'm happy to grow into nicer cash flow. 

You'll need more than just the DP, there are closing costs, initial repairs (there's always something), and some money set aside as reserves.Post the details and the community will be happy to take a look.