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<<In what order should someone withdraw from their retirement savings, assuming that they have a regular IRA, Roth IRA, regular savings, and an annuity that is still in accumulation phase?>>

Don't know about annuity, don't have one, won't have one. Of the remaining three, I'd take from regular savings first if you haven't reached the age for "have to" start withdrawing from regular IRA. This allows the regular IRA to grow a little more tax deferred where your regular savings is being taxed anyway. I'd withdraw from the Roth last because of the "tax free" status and ability to pass it on to others and keep the "tax free" status for them.

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