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 not properly model an updating agent choosing even after seeing even, it models an updating agent choosing even without having seen anything.
An obvious simplification of an (computationally extremely expensive) updateless agent would be to simplify X. If X is made up of the parts X1 and X2 and X1 is identical for all instances of S being called, then it makes sense to incorporate X1 into a modified version of S, S' (more precisely the part of S or S' that generates the world programs S or S' tries to maximize). In that case a normal Bayesian update would be performed (UDT is not a blanket rejection of Bayesianism, see Wei Dai's original post). S' would be updateless with resepct to X2, but not with respect to X1. If X1 is indeed always part of the argument when S is called S' should always give back the same output as S.
Your utility implies an S' with respect to having observed "even", but without the corresponding update, so it generates faulty world programs, and a different utility expectation than the original S or a correctly simplified version S'' (which in this case is not updateless because there is nothing else to be updateless towards).
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.)