1. You may or may not be required to pay estimated tax as Fanfare states above. However, the IRS philosophy is that estimated taxes should be paid when you make money. If you owe over $5,000, that is considered a substantial underpayment. You may get a great job and withholding the extra tax from your paycheck could rectify the situation.
2. No. Take a look at the sch D tax worksheet and you will see the hard numbers.
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