Hyperborea:The riskiest years are likely to be the early years. If the early years bring good returns then the likelihood of outliving your portfolio decreases. If the early years are bad then the likelihood of outliving the portfolio increases. With either case there is still no guarantee just probability. Changes made in those early years (income increase or withdrawal decrease) will have the most effect on survival.

I always appreciate your math-grounded approach to SWR's and retirement. It's so refreshing to work with logical assumptions and real numbers rather than emotions about what will last.

My feelings about how much is enough is pretty similar to yours. I think the risk of continuing to work is as great as the risk of running out. Primarily because you can always take steps to avoid running out, but you can't go back and start earlier if you worked too long.

I think for many periods a WR of 6% or more will be succesful, you just won't know until that period has already passed. But, you can start out at 4% and adjust up, or you can go with the method you suggest.

Being conservative is a double-edged sword. I think it is smarter to be daring when you choose to retire (do it early!) and then be conservative with your money after you retire to make sure it lasts. For example, if you find that healthcare is eating you up then get a PT job with health benefits. There is so much you can do after retirement to control your expenses that you don't have to sacrifice another year of your life just to be 'conservative.'

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