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Greetings, Jonny H, and welcome. You asked:

<<It's time to set up that Roth IRA before I have to start paying taxes again (I live and work outside the US). And I just realized how much Datek (I've been using them) charges to watch over an IRA compared to other discount brokers.
So I narrowed it down last night, and it looks like Suretrade has what I want. Dateks sez no fee to transfer in and out, as does Suretrade. And Suretrade doesn't charge for IRA maintenance.
But how difficult or possible is it to transfer (about)$4,000 worth of stocks I already bought into a Roth IRA account?>>

Unless those stocks are already in an IRA, you can't do it. Ordinary annual contributions to any IRA must be made in cash. If, though, you are talking IRA, it's merely a matter of asking that the shares be transferred directly from the traditional IRA custodian to the Roth IRA custodian. Declarable income will be based on the market value of those shares as of the transfer date.

And BTW…. You also cannot put more than $2K into a Roth in a year unless you are rolling money from a traditional IRA or another Roth IRA. You could, though, put $2K in your Roth and another $2K in your spouse's Roth.

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