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Greetings, GreggN, and welcome. You asked:

<<I've been reading quite a bit about the Roth IRA setup and understand the contribution rules for the most part, but one answer (clarification?) still eludes me: If you are not starting the Roth IRA with money from a traditional IRA conversion, how much can you put in the account when you start it?>>

If you have the earned income to do so, then you may contribute up to the maximum $2K for the year on opening the account.

<<I'm not clear on whether an 'initial' contribution is the same as that year's 'annual' contribution. Or, would it be analagous to opening a brokerage account (which theoretically have no upper limit) and then converting that account to a Roth IRA?>>

If you intially contribute the full $2K allowable for the year, then that's the same as the "annual" contribution. If you initially contribute less than $2K, then that becomes the annual contribution only if you elect not to contribute more to use up the full $2K that's allowed for the year.

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