In my experience, it really depends on the size of the property and your comfort with tax details.

@Amy Houghton The STR tax loophole generally does not apply to midterm rentals which are typically leased for 30 days or more.

If one has a second home in a high-tax state that rents for more than 14 days a year and is used more than 14 days, would it make sense to convert it to a rental property, given the new tax law?

I am wondering, is that the most Tax efficient way moving forward as I purchase more properties and forms more LLCs?

"Tax the rich" = send money AWAY! 

Your CPA is likely concerned about the Personal Use Limitation, which is the biggest threat to the STR tax strategy.If you used the property for personal purposes for the greater of 14 days or 10% of the total days rented during the year, the IRS classifies it as a "residence."

Hi,  Any advice  I live in Texas, my portfolio is increasing in value and so are my property taxes This is despite contesting them yearly. at the same time recent new construction of Class A multifamily properties  have pushed my rents down.   

Good tax advice isn’t cheap.

Seriously, the whole strategy hinges on proving Material Participation so you can claim those juicy tax losses against your active income.

You might want to see if you are eligible to treat the property as active instead of passive.This might result in a large tax refund.Best of luck!