As people tend to forget, the law of physics dictate that the same causes have the same consequences.

Using a GC you will have less headaches as you'll have one point of contact and they will coordinate schedules between the various trades. 

Default Consequences: If the husband defaults on the HELOC, the lender can pursue the property as collateral.

Failure to comply with a court order can have severe consequences. 

At $377K/door, this building's costs will be nearly 2X what a similar building would trade for in this location.  

They have nothing to lose, its like giving someone a free ticket to the football game, if they go great if they do not who cares they just do not go and there is no consequences for them. 

My thought is is use the Rent Ready feature of reporting his payment history to the credit bureau so it can work in his favor as a trade line, but I'm wondering if this is an unnecessary added step since he can already pull transactions on his bank side. 

You mentioned a career change, I think going into the trades like plumbing and electrical are great and you can make good money doing those, but I think you may be taking on too much by trying to do that right now.

The trade-offs are real, but for consistent cash flow and the right landlord, it can be an excellent strategy.What’s the best way to start?

What do you use for skip trading and how accurate is it?