(The exception would be the rare deal where the property changes hand for a price far below real market value).The sub to or wrap adds a certain degree of ADDITIONAL risk of failure.  

I hoping this role will help me get my feet wet in the industry and give me a chance to learn the ropes while building valuable connections.

Although he is a banker, he thinks having the ability to operate as a broker and place loans with 30+ other lenders, in addition to his bank, is the "best setup."

Additionally, you may wish to speak with a CPA as to whether or not becoming an S Corp is the right decision – they can assist with reducing self-employment taxes.

There is some additional information that wasn't mentioned in your post above which sheds a different light on the situation.  1.

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.

If you feel ambitious, you could try a BRRR strategy adding additional equity to the subject home and then taking equity out of it to pay off either the HELOC or if you decided to the refinance the primary residence. 

When analyzing a market and breaking it down into property Class submarkets, do you find it helpful to complete this division at the city-wide market level, or do you find it also beneficial to additionally break it down by suburb, and even neighborhood?

This poses an additional challenge for new RE investors.  

She'll help you arrange where the furniture should go, and links to any additional accents she recommends (rug, curtain, curtain rods, accent tables, etc)