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Is it a good idea to contribute $2000 to the Roth IRA in one lump sum or should I do $166 a month for the whole year?

Generally, the sooner you contribute, the better. On average, the market tends to go up (somewhere in the neighborhood of 11% per year). By waiting, you allow this money to grow unsheltered and expose yourself to unecessary taxes on the gains that occur while you're waiting to deposit the money.
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