Technically speaking this would be my secondary and I would be in it for a very short time (month to month and a half), but I do not want to go through the entire process only to have it fall through.

Technically your net profit would be the sale price including closing costs minus your total "all in" cost to put the property in service.

As a matter of fact your transaction does technically meet the time period suggested by at least two court rulings where they attempted to describe an appropriate holding period as two tax years and two calendar years. 

The other area that tends to bite us in the *ss is not doing real technical and legal due diligence on your PMs and GC.

Technically you could make zero dollars a month and still have a net worth of a million dollars or more.

It is not 'technically' a title transfer that would trigger a transfer tax. 

While technically it would be an expense, the person I am borrowing it from wouldn't be claiming anything on their taxes or providing me any kind of tax forms.

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. 

Licensed agents are not technically allowed to wholesale.For me I never need an agent cause everything is on standard contract, even contracts I work out with wholesalers.

Technically you can not.