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(Not much in Roths, as we haven't been eligible for many years).

If you don't have any pre-tax IRAs, and/or you don't mind converting those pre-tax IRAs that you have to Roth accounts, you could have been doing 'back-door' Roth contributions for a few years now, where you contribute to an after-tax traditional IRA and convert immediately.

Back in 1999 I did leave my company for a short while, and when I returned I was able to just restart depositing into the same 401k account.

How long was 'a short while' compared to the 5+ years you anticipate taking off this time? Have your company's employment rules and/or 401(k) rules changed in the ensuing 14 years? Will the rules change in the next 6 years before you take off? Or the following 5+ years before you return?

Making the assumption that your experience upon your return in 1999 will be the same as what you would experience upon your return sometime in 2024 (or later) could throw a wrench in your plans, if the assumption is incorrect.

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