While he has helped millions become debt-free, which is amazing, I'd seriously challenge how many he's helped become wealthy though (his philosophy doesn't teach how to build generational wealth). 

I’m working with my father on managing his RE portfolio.We have one multi family property that is fully paid off and generates roughly $200k in NOI/Cash Flow.

To remove the rental income generated to me personally and have it towards an LLC. 

If you had a property that was treated as a rental and it was placed into service, you should list it on the tax return.Rental properties within the first couple years, as you stabilize the property, normally generate a tax loss on the return.Whether you can utilize the loss on your return, as it may be considered passive, is another discussion.

I’m a second generation rental owner.

We're all here to generate more income, and we should all do what makes us feel the most confident be it turnkey or "traditional" soup-to-nuts.Regarding #2, of course the turnkey company takes a cut, but to me that matters not if they are getting you a better deal than you could find on your own.So my request to you... can you keep us posted over the coming months how everything turns out?

My goal has been to borrow money for the rehab, rent it out to generate income for the Trust's beneficiaries, and then do a cash-out refi to recoup my down payment and any other out-of-pocket expenses.I believe there are limitations in an Irrevocable Trust, which would prevent me from simply deeding the property to myself or possibly even to an LLC if I create one, even if the end result is in pursuit of my fiduciary duties to the beneficiaries, as Trustee (i.e. making the home inhabitable and generating rental income for the beneficiaries).

Option 2, you risk $30K with the belief that the unit will begin generating some free cash flow. 

That all revenue generated would have to stay in the company and couldn’t be used for personal things.I’m trying to find a way to use my God given talents and the only one I seem to have is in Real Estate hahaha.

You may be entitled to taking deductions used to generate your income.