I own a property in Westchester County that i would like to convert from my primary to a rental. I have lived / owned it for 5 years with my wife. Based on recent sales in the area i stand take a $50-$100k loss if i sold. How long will i need to rent the property before i can sell it and realize the benefits of any loss associated with a sale - assuming their is no meaningful market recovery.

From a tax calculation perspective what % of that notional amount will i actually realize - will it be my tax rate times that notional loss.

Further what is the process from a documentation perspective to convert the property so once i sell it at a loss i can provide proof it was a rental property to NYS and IRS.