I think self-confidence and not trying too hard to please everyone are admirable qualities in games as well as people. Not advocating arrogance or insensitivity - those are the mirror universe versions of the qualities I mean. Pretty much like Kirk and the mirror Kirk.
To continue the analogy between games and people, the (possibly unfortunate) fact is that desperation tends to be unappealing. So a game that seems desperate to please may be off-putting for that reason...
Throwing in psychology, meaningful relationships practically depend on requiring one to adjust something about oneself; they are forged when we willingly step out of our comfort zones into somewhat unknown territory in order to approach more closely something or someone that attracts us.
But this cannot happen if the person or game pre-empts that personal investment by being too "user-friendly". I know the intentions are good and I am not for user-unfriendliness. Again, that is the mirror universe exaggeration. But I think we all know (or can imagine) how oppressive it is if someone is constantly checking that your every need is met - including imagined ones.
"Are you sure you are perfectly comfortable even though you do not have a glass of water?" The chances are they would have been, had it not been for this question. Not making such offers is not inconsiderate - it is considerate because you are respecting the other individual's personal space and placing that before your own need to show overt consideration.