9) adding multiple ADUs or adding an ADU to a quad looses F/F conventional financing.

Proc. 2013-13, 2013-6 I.R.B. 478 (February 4, 2013)Report on Schedule E, not Form 8829Allocate expenses if managing multiple propertiesCaution:   those Home Office Deductions cannot be used to increase your losses!.

Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

Additionally, ATCP 134.05 says that if the tenant provides a consumer credit report from an agency that compiles and maintains files on consumers on a nationwide basis and it is less than 30 days old, the landlord may still run a credit check but at its own expense.When I inquired with the company, they replied: "These laws are in place to ensure that you, as a landlord, are not profiting by incentivizing multiple applicants to apply when you have no intent to rent to them.

I have just read a book about this, and a business owner spoke about his employees who would take "multiple taxi trips in one day" or "dine at the most expensive restaurants even when alone" its just something that will happen.

This would be running multiple proformas based on each scenario.

Hire an accountant—but maybe not for $6,000/yearA real estate tax pro can help you save money, but $6K a year is way too much unless you own multiple properties.

I'd start small and just try to learn the game of flipping. 

If I would have bought a sustained portfolio with multiple units rather than starting with a single purchase I truly believe I would have lost a lot of money while my systems flailed rapidly attempting to catch up. 

A cheapo Walmart junk lock is not the same as a Kwikset (which is honestly not that good a lock anymore), and multiple keys is not the same as one key.