It is somewhat complex to try to explain on a forum, but at a high level, you (aka GP) and your family member (aka LP) would agree on how much the 2 of you would put in for the amount of equity needed (usually expressed as a %).

The regulations provide both insight and ambiguity.25% or more owner of the entity; OROne who exhibits significant control over the entity.

I'm from Leesburg, and I can tell you—multi-family is a solid choice (piggybacking the previous comments which I agree 💯), especially with that live-in/rent-out, house hack strategy.

I agree with @Collin Hays its a trust issue. 

I agree in doing a cash out refi.

I agree, it could be possible but I have yet to see a deal that really works when the borrower is borrowing 100% financing on a deal as the lender is going to have much higher rates and default rates.

I agree with Greg, one lesson is to do everything yourself.

So once you’ve approved a tenant at an agreed rent, it goes to the authority….

But I agree with your initial statement that when you sell to yourself, you don't need a NEW title search or NEW title insurance. 

I agree very market dependent.