as an updateless decision maker you don't know you are in the branch where you replace odds with evens.
I don't understand what this refers to. (Which branch is that? What do you mean by "replace"? Does your 'odd' refer to calculator-shows-odd or it's-actually-odd or 'let's-write-"odd"-on-the-test-sheet etc.?)
Also, updateless decision-maker reasons about strategies, which describe responses to all possible observations, and in this sense updateless analysis does take possible observations into account.
(The downside of long replies and asynchronous communication: it's better to be able to interrupt after a few words and make sure we won't talk past each other for another hour.)
Here's another attempt at explaining your error (as it appears to me):
In the terminology of Wei Dai's original post an updateless agent considers the consequences of a program S(X) returning Y on input X, where X includes all observations and memories, and the agent is updateless in respect to things included in X. For an ideal updateless agent this X includes everything, including the memory of having seen the calculator come up even. So it does not make sense for such an agent to consider the unconditional strategy of choosing even, and doing so does no...
Consider the following thought experiment ("Counterfactual Calculation"):
Should you write "even" on the counterfactual test sheet, given that you're 99% sure that the answer is "even"?
This thought experiment contrasts "logical knowledge" (the usual kind) and "observational knowledge" (what you get when you look at a calculator display). The kind of knowledge you obtain by observing things is not like the kind of knowledge you obtain by thinking yourself. What is the difference (if there actually is a difference)? Why does observational knowledge work in your own possible worlds, but not in counterfactuals? How much of logical knowledge is like observational knowledge, and what are the conditions of its applicability? Can things that we consider "logical knowledge" fail to apply to some counterfactuals?
(Updateless analysis would say "observational knowledge is not knowledge" or that it's knowledge only in the sense that you should bet a certain way. This doesn't analyze the intuition of knowing the result after looking at a calculator display. There is a very salient sense in which the result becomes known, and the purpose of this thought experiment is to explore some of counterintuitive properties of such knowledge.)