Note that my attorney believes the NC Banking Commission would rule this way, your state may have other regulatory and case history that your closing attorney can investigate.

It is advisable to do your due diligence and ask about such things as how long have they been in business, are alternative assets their sole focus, are they BBB accredited and rated, are they a regulated financial institution, have they ever been sanctioned by any regulatory bodies, how many accounts and how much in assets do they administer?

Neither seems quite right, which for me, is often just an intuitive feeling, but it drives me to generate other options.I know renting something is a long term passive income kind of goal - but are you even sure that you won't run into any regulatory headwinds in having the second house on your existing land? 

But that is a bit far off and still needs to go through the regulatory process.

My guess is this might be frowned upon by government regulatory institutions - but I don't know.

If he has valid comps in your area sold in the last 6 to 8 months...sounds like you can make a complaint to his licensing regulatory body.

If your girlfriend contributes her commission, as opposed to lowering the price by that amount, which wouldn't reduce your down payment, it will be taxed income to her.Your exit strategy of selling to a wholesaler is crazy, they'll pay you about 70% of value.If you're going to charge market rent, and trying to push taxes and insurance on the buyer/renter....good luck with that, outside of any regulatory issues.You'll have closing cost on both transactions, and unlikely a seller credit will cover them all on the front end.This idea just has too many problems.

@Anil Samuel   passing the exam is regulatory and has very little bearing on how well you will do as an agent. 

A note buyer inherits the type of note and regulatory requirements from its making, regardless of that attorney turning a blind eye, you go to foreclosure you can only seek amounts due and costs, it could sell.

The government/regulatory level of respect for self-employed/business owners is slim to none.