You can't conclude this
Yes you can. The real calculator in the real world had a 99% chance of being right. The counterfactual case is (in all probability) the 1% chance where it was wrong.
Nah. See, given that the real calculator says "even", there's a 0.99% chance that it's correct and that, in a repetition of the experiment, it would say incorrectly say "odd". There's also a 0.99% chance that the real calculator is incorrect and that, in a repetition of the experiment, it would correctly say "odd". The counterfactual case is just as likely to be the calculator being correct as the calculator being incorrect.
ETA: The above is wrong. I was confused about the problem because I wasn't thinking updatelessly. It's like Newcomb's problem.
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.)