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The easiest part of your question is the transfer. To transfer an IRA to another custodian, contact the receiving custodian. Usually there are a few forms to fill out and they take care of it for you.

Presumably if you transfer the back loaded mutual funds as shares, you will wind up paying the backload to Dean Witter--but I would think when the shares are sold, not when they are transferred. Ask Dean Witter.

The tax question arises only in the case of the Roth conversion. When or if you do the conversion, you will pay income taxes on the cash value of account. The conversion is more attractive if you can do it at low tax rates. If the account is large, conversion may be prohibitive because the conversion alone can put you into upper brackets. But others on this board may have other thoughts.
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