Then ask why the property tax rates for hotels on Maui hasn't increased in over two years, yet they continue to raise it for STR's as well as non-owner occupied residential properties.

Alternatively, you can use the fair market value of the home at the time of conversion"Keep in mind, you will probably want to talk to a tax professional to go over all the consequences. 

@Jonathan Greene  I'm selling older properties, one recent sale was built in 1890 for example, selling all townhouses, all semi-detached, all rental condos, vacant lots (no income), and most multi-family properties. 

I rather not put them in but I also don't mind the extra income for the occasional phone call to the appliance technician.

They handle all statements as well as tax forms. 

As in some loophole that allows investment in real property through a tax exempt entity?   

Understanding the potential rental income is crucial in assessing the profitability of the investment.Expenses: Do you have a clear understanding of all the expenses associated with owning the duplex?

Had I listened to their advice, I'd be in a much lower tax bracket and have a much lower net worth. 

However, given that the STR it is technically ‘attached’ to my Primary residence, could I still offset loss years against my W-2 income?

These loans only look at the income the subject property is bringing in.