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1) Hire a CPA. A good one will save you far more than you have to pay him
2) Pay quarterly ONLY if you can't trust yourself to not spend the money during the year. The underpayment penalty is so low that it's actually profitable to just hold the money until April 15 and pay then.
Again, I can only advise this if you trust yourself not to blow it and then not have the money to pay the piper.
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