He even trains IRS agents, usually in the course of an audit when he's called in to rescue someone and has to teach the IRS agents the CORRECT way (as established by the courts) to interpret the tax code.

No audit is needed. 4.)

They are usually triggered during an audit or if you change the insurance policy, that's why I usually recommend keeping the existing policy under the seller's name and adding your new policy on top. 

I also got to thinking that we should perhaps audit each of our units before each winter to see what components/tenants could be eligible which would have otherwise been major capex items. 

Rather than start out new books with a CPA, I'm hoping to hire an accountant for a financial audit going as far back as possible, to confirm the unfortunate workflow (expenses paid from various personal accounts, unreliable reimbursements from building accounts, etc). 

Under audit, the IRS may view your cash-out refinance as you taking cash at closing, which is also a taxable event.

Now I am not impartial to Sub2, after all I did write a course on it and have purchase a ton of houses using the method...

The Buyer(s) & Seller(s) nor their Agent(s) listed below have any agreements (written or implied) that will allow the Seller(s) to remain in their property as renters or to regain ownership of said property after the successful execution of this short sale transaction.†HUD/FHA/VA, Fannie Mae, Freddie Mac & FDIC are now carefully auditing short sale transactions going forward and are also looking at past closed short sale settlements that may have been considered non-arm's length transactions.

If there was an audit by one of the GSEs they wouldn't see the entity owned the property either.

The IRS leaves everything up for interpretation, you would have to prove your not disqualified by an ERISA attorney letter which no attorney will sign off if audited Seems crazy but If it's a gray area probably not a good idea