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The decision about whether to rollover your 403(b) money to a traditional IRA should be made based on:
- what it would cost you in fees and penalties to exit any 403(b) investments that have those fees
- whether investments in the 403(b) have high maintenance or annual fees
- whether you can get better investments in the 403(b) or on your own. In some 403(b)s, all the investment options are much worse than what's available to the general public; in others the investment choices are much better than retail.

It's a separate decision as to whether to convert a Traditional IRA to a Roth IRA. This should be based on your expectation for whether your tax rates will be higher in the future.

The best time to convert is when you can scrounge up enough cash to pay the taxes, but are in the lowest possible tax bracket.
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