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<<<How difficult is it to find a custodian to handle DRIP plans for an IRA? Are there any online brokerages that will do this, if the first shares are purchased through them?>>

These will not be DRIP plans per se. Instead, the brokerage will reinvest dividends and capital gains by transferring at current market value shares in the same stock the brokerage holds in its own inventory. Fees may be involved, and the only one I know for sure that does this is USAA Brokerage Services. >

When I had an account at the shallow-discount broker, Fidelity, they did this for free, too (if you do not consider their relatively high commissions as an unnecessary cost).
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