If I can make it work, it would save me a substantial amount of taxes.I would then plan on taking those funds (profit from the flip) and either (a) investing it in other self directed eligible assets (RE, LLC interests, etc.) or (b) transferring it back to a traditional brokerage firm and to simply invest it in equities.  

Any attempt at a prescriptive time line is simply not true as a rule. 

In a jurisdiction where you can set policies to preclude having your unit approved by the welfare office it is a no brainer to simply avoid renting to S8. 

On show 325 at 1:27:00 he mentions a web service (padlock.com) where you can enter an address and buy the owner information like phone number, loans on the property, ARV, etc....   

Simply, there's not a ton of deals here that I'd be able to get a loan for (mostly based on my income rather than down payment) and the ones that I can afford/qualify for are generally in neighborhoods I wouldn't feel comfortable living in. 

The person doing it for me will not be making any money off this transaction and will simply be doing this as a personal favor to me, and I just wanted to clarify the tax ramifications, if any, for both of us. 

It is up to us to dig in deep, ask them the hard questions and learn everything we can about them BEFORE entering into a contract with them.

So again, sell as yourself, sell as himself, buy as a disregarded LLC - this technically does not change the taxpayer and would be permissable for 1031 purposes.I always counsel you to make the deeds match as closely as possible simply because it avoids questions and fluke situations with inexperienced field agents in an audit. 

So there's simply no comparison. 

@Geoff Garber you need to make sure the deals you enter have enough meat on the bone to go around.