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1

Income tax withholdings are only "optional" if you expect to pay no income tax for the entire year (and the previous year). Other than that, the W-4 you fill out gives you a reasonable number of allowances to declare to determine how much tax (if any) should be withheld. They are fairly accurate unless you have unusual circumstances like uneven income, ...


3

New York State income tax makes no distinction between capital gain income (long or short) and earned (wage) income. As you've noted New York City has an additional income tax on top of the New York State income tax. The State And Local Tax (SALT) deduction applies to the Federal itemized deduction, and starting for the 2018 tax year capped at $10,000 USD. ...


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