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curious if where would you fit 529s in this waterfall?

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There is some nuance and state level differences, but overall I would probably have it as a fork before the taxable account. I would also have a cap at the total amount I would want in the account and by what age. For example my end goal is to fund 50% of college via a 529. That would require somewhere like $75k total at 5 years old.

I need a dedicated 529 article eventually!

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dedicated 529 article would be great. I am especially trying to get a better understanding on recent rule changes on 529->Roth rollover.

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If planning to switch jobs midway through year, reversing “finish maxing out 401k” and “mega backdoor Roth” would switch to take advantage of both company matches, correct?

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Correct. You can double dip on the Mega-Backdoor, but the Pre-Tax 401k contribution is across employers. So you would want to save some space to get as much match at both companies.

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