I still plan on house hacking at least one more time but one thing to keep in mind is sometimes life happens and tenants can’t pay on time.  

Bottom line is that you may put yourself in a situation where the best way to maintain your tax efficiency is to keep your investments foreign for the long term. 

You should keep a record of the date you make the request.Are calls from political organizations or calls soliciting for charities covered?

I own 1 profitable rental property and I am retired, keep separate records on my rental property.According to IRS guidance it states:  "If an interest in real estate fails to satisfy all the requirements of the safe harbor, it may still be treated as a trade or business for purposes of the section 199A deduction if it otherwise meets the definition of a trade or business in the section 199A regulations."

I have been all over the Yucatan and Tulum keeps calling me back. 

If you set it up with a car rental service like Turo are likely protecting yourself/car more from potential issues and damage and may be able to keep it off platform and only make it available to your renters (not sure on that last part but just a thought).Also, from a lender perspective it could complicate things if you are looking to refinance one day and have car payments included in the lease payments/on the lease.

Keep searching and learning.Hope this helps some. 

But, if you keep up a pattern of switching farms every 8-15 months, my guess is that at some point you begin to raise red flags. 

With that being said this would be my second project, but I keep running into problems when going for a loan to buy the multi-unit.

Thanks I'll keep this mind.