I have other HELOCs that were much easier to get both personally and professionally.

I don't know if they still do it but if memory serves a few years ago TD Bank would do a HELOC on a rental in second position but only if it was titled in someone's personal name. 

What appears to be great "curb appeal" to one person might be overwhelming to another. 

Gordon is the owner, I doubt whether he could completely hide behind his LLC to protect personal liability. 

HELOCs are generally provided to properties that are held in the owner's personal name.Are your family members not interested in refinancing the property?

I will caution you that if they pull something like this and you immediately start offering any concessions as is repeatedly addressed above - this type of personality will make note of that and the threats will be ongoing for the duration of their tenancy.

A duplex strategy is a low-risk entry, saving on living expenses.

The person worked for H&R Block, now works for TurboTax Live and is being honest about their skills: NOT QUALIFIED.

Do you rely more on the deal itself or the person behind it?

If you’re looking for short-term cash flow, you might need to explore nearby markets with lower entry costs and higher cash-on-cash returns, even if they aren’t as familiar to you.