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I'll probably retire at 65, though The Plan is to move out of the private sector and into a teaching job once it's feasible.

So it sounds to me like what you need to know is: 1) how much you project that it will cost you to live during retirement, and 2) how much income you have to spend in retirement. Once 2) exceeds 1), you are ready to retire.

Given that, I would not try to convert the annuity-type retirement benefits (social security and defined benefit pension) into an equivalent lump-sum. Instead, I'd total your accumulated assets, calculate what spendable income would result from that total (based on estimated earnings and your willingness to invade the principal), then add in the SS and pension. That would give you your total income in retirement.

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