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No. of Recommendations: 2
Two points, two kudos and an observation:

First the kudos:
- to RHinCT. I'd not seen the article before, and I like it.
- to AdrianC: likewise, the portfolio backtest tool

The points:
1) yes, the Alice/Bob comparison neglected the 30-year parameter. I think of the 4% rule as being the answer to the following question: In the modern era (say, since 1929), what did the first generation of literature to examine this question conclude was the steady withdrawal rate from a(n approximate) 70:30 portfolio that allows the near-certainty of not going to zero over the ensuing thirty years?. The phrase "Alice is 5 years closer to death" may not be quite accurate (both Bob and Alice will be five years closer to their obituary in 2035 than in 2030, but we have no idea of either's life expectancy), but yes: Alice has burnt through 5 of the 30 years of the question.
2) I stand by my sequence of returns point. It's not that Bob is withdrawing more than Alice: both are withdrawing 4% of their retirement portfolio as it stood the day they retired, adjusted annually for inflation. Instead, it's that Bob -- retiring after an impressive five-year runup -- is, as long as economic cycles remain a thing, statistically at a higher risk of a dismal few years coming up in the early part of his retirement.

That brings me to my observation: take one of the more nuanced retirement simulators. Adjust all of the toggles to give a portfolio with a 95-98% chance of a 30-year success. Repeat with different inputs, as long as you get a 95-98% success rate. Then, isolate and consider the 2-5% that failed.

Almost uniformly, those will be portfolios that had several very bad years during the first five years or so of retirement.

That's Bob's problem. With her early run-up, Alice is in a much safer position. Bob, statistically-speaking-and-as-long-as-economic-cycles-remain-a-thing, is more likely to turn the corner a mile from the trailhead and find a bear.

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