My understanding is that O.J. used asset protection trusts established in Nevada with spendthrift clauses to protect his assets from creditors...   

someone could leverage 20,000 in bills every month and keep it against there debt vs giving it to banks/retail/ or other fine establishments and paying cash.

I am going through the regulations and restrictions in that place (not a closed community but there are some rules).

In your opinion, what is the most effective way to establish an LLC? 

I find trying to slog my way through government regulations to be a bit overwhelming.

It's not a get rich quick scheme, it's a lot of active work and I would have 5 yrs in my head at a minimum before you truly become established and stabilized. 

Additionally:Is there a specific state where it makes more sense to establish the holding company (now that anonymity in states like WY or DE isn’t the focus)?

We can't HELOC due to TX regulations and cash out refinance doesn't make sense with interest rates.

Trusting a GC can work if you thoroughly vet them, use a detailed contract with clear milestones, and establish systems for accountability.

I invest out of state in Pittsburgh from DC and self-manage everything, but it's taken me years to establish the right contacts, develop seamless processes etc. that allow me to handle everything remotely with confidence.