I don't think that that's a bad thing. The immortal starfarers necessarily go somewhere; the status game players don't necessarily go anywhere. Hence "winning". The point of the post was to warn that not only answering our questions but figuring out which questions we should ask is an issue we have to tackle. We have to figure out what winning should be.
The reason that the immortal starfarers are better is that they're trying to do that, so if all values aren't created equally, they're more likely to find out about it.
However, it is important to try to determine whether someone is a clever arguer or a curious inquirer when they are trying to convince you of something. i.e. if you were in the diamond box scenario you should conclude (all other things being roughly equal) the curious inquirer's conclusion to be more likely to be true than the clever arguer's. It doesn't really matter whether the source is internal or external. As long as you're making the right determination. Basically, if you're going to think about whether or not someone is being a clever arguer or a curious inquirer, you have to be a curious inquirer about getting that information, not trying to cleverly make a Fully General Counterargument.