If I’m looking to purchase a property that needs a significant amount of work, (1) how do I, an amateur, even identify what needs work?

Truth is we strive to identify those quickest possible and say it's not a good fit and let them go, it's rarely taken well "what, so, so your firing ME, who the hell do you think you are". 

The breakdown is below, hopefully, that will help you identify where the numbers are diverging. 

Who can help me identify the plumbing and perform full installation?

Have you ever heard of an agent being engaged partially at reduced rates - just to help with the documentation without the marketing or identifying buyer?

I was starting to have 2nd thoughts.The first 1031 exchange deadline is to IDENTIFY the property or properties to exchange into.

So the due diligence in these areas is really double - You've got to identify the areas for each and the pricepoint and types for each in each area. 

So rather than say MN, which can be anywhere from International Falls too Chippewa Falls and everywhere in between, identify the geographic rings of viability, a primary interest area, secondary, and consideration. 

I understand you're a wholesaler and identify distressed/under-valued properties, but how is $20k of value being created with no improvements?

The type of self-directed IRA that will best suit your situation and goals will drive the process of identifying the right firm to work with.A self-directed IRA custodian is a processing entity.