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[USA] Is there a decent calculator that can help me estimate my taxes for different scenarios?
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I don't think you'll find a free, ready-made tool.
The easy solution is to get a commercial tax package like TurboTax and run different scenarios.
The other option is to make a big spreadsheet that mimics the tax forms, with linked cells and logic to match the instructions on the forms. It's very time consuming, but at the end you will understand your tax situation much better because you've sifted through all the details.