I have been researching dielectric unions like crazy today, but I'm very grateful for the tips received here!

Cash offer do carry weight as they can close quicker, don't need appraisals etc, but as an agent that works with buyer and sellers, I've seen it many times where a seller will pick a different offer due to some connection to the buyer (ex military, young married couple just starting etc) They want to know its NOT going to an investor specifically. 

You can go to local Credit Unions (CUs) and banks to get this LOC. 

A lot of 2-4 units over that way and some great TLC properties that are priced in favor of the buyer & cash flow.I was just looking at a few properties over off of Union the other day.  

Should I be contacting expired listings on the MLS, foreclosed listings, distressed sellers etc … Also does anyone have recommendations on how to build relationships with banks, credit unions, investor-friendly title companies, contractors, appraisers etc?

The Palmetto, Sandtown, Union City areas are kinda overlooked but still has a Southern draw that you don't find in the inner city.

Reach out to a variety of lenders, as banks, credit unions, private lenders, etc., all have varying terms.

I would find local credit unions or small banks, essentially portfolio lenders who hold the loans in house.

We just started talking to Josh Gilmore from SDIRA Wealth to invest in Real Estate.  It seems like it is so much easier to work with a company than to try and do it ourselves.  We live in New York and there are really...

This is probably a tougher one considering most Hard Money / Private lenders that are go-to for BRRRRs like this focus on residential only - your best bet might be private money found here or in person networking or a local bank / credit union.