You can contribute as often as you want, up to the maximum amount. You can make a lump sum end-of-year contribution, or set up automatic monthly or semi-monthly withdrawals from a checking or brokerage account into the Roth IRA accounts. Check with your custodian to see if there is any fee involved.
Depending on custodian minimums, you can contribute either way. And, you don't have to deposit more than $2,000...but small accounts can be subject to greater fees.
As a reminder, you are limited to your earned income or $5,500 ($6,500 if age 50 or older) whichever is less.
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