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Investors & landlords
@Shuja not wanting to beat a dead horse and having gone through replies from @Hal_Al and @Carl , here is something to consider :
(a) the purpose of the rule by the IRS is to tap into the underground economy --- where small independent workers earn an amount but do not report the income on their returns ( actually , as a volunteer to the treasury I heard this being discussed by Neena Olsen, the taxpayer advocate, when she visited Argentina and learned how there each and every sale results in a tax receipt that both the buyer and seller must report -- thus cutting off the grey economy ) -- thus not paying the IRS and the State and also not paying the 15.3% net to the SSA
(b) what IRS is trying to do is make you responsible for ( and paying the extra 15.3 % that the worker would have to pay when income reported ) being their watchdog -- especially since the rule applies only for payments to independents ( presumed to be untrustworthy in the land of innocence till proven guilty ) but not to businesses ( whom are always to be trusted because they probably know better or have CPAs involved , whom are surely trustworthy, never mind that almost all the tax-preparers sanctioned by the IRS are all CPAs
(c) As @Carl mentioned , you employed a person to do the work, you paid them and really , how he/she does or does not report the income really is beyond your control unless of course you choose to pay extra ( because the worker surely will have to charge extra for the privilege of paying SSA )
But you are correct that the rule ( not the law ) requires you to issue 1099-misc and TurboTax as a responsible service provider has to ask the question.
that is my view