>for example, in his book "Mere Christianity" he explicitly supports reactionary Christian teachings during the war. When more forward looking writers were talking about new takes on sexuality and women's rights, he was still saying woman should be subservient and that homosexuality is unnatural and sinful.

Those were very common beliefs among his generation. Penalizing someone as "not a diverse reader" because they didn't join the leading edge of cultural progress on those issues would disqualify the vast majority of readers of every time period. I don't think you can't draw any conclusions about his reading history from his cultural positions. All you can conclude is that he wasn't progressive.

>I would just expect someone who is so well read to have some sort of proactive view on social issues, especially considering the time he wrote the book was a period of social upheaval. Instead of understanding and considering the new morals of the generation, he doubled down on ideas and principals that quickly become dated, now bordering on nefarious.

That may be your expectation but I would disagree that it's applicable to general populations (or even educated/"intelligent" populations). I certainly don't think it's an adequate foundation to argue that Lewis "wasn't a diverse reader." And the only reason I'm harping on this is because you specifically said "he is bad at contextualizing and deconstructing his arguments"...but I don't think your argument about his reading is a whole lot better.

>I love Narnia, but he himself has awful takes when it comes to social structure and rights.

I would counter that his takes on homosexuality and women were less egregious than you remember, though of course they're not "modern" in nearly any sense of the word.

https://spiritualfriendship.org/2013/08/23/c-s-lewis-on-homosexuality-and-disgust/

>There is much hypocrisy on this theme. People commonly talk as if every other evil were more tolerable than this. But why? Because those of us who do not share the vice feel for it a certain nausea, as we do, say, for necrophily? I think that of very little relevance to moral judgment. Because it produces permanent perversion? But there is very little evidence that it does....Cruelty is surely more evil than lust and the World at least as dangerous as the Flesh. The real reason for all the pother is, in my opinion, neither Christian nor ethical. We attack this vice not because it is the worst but because it is, by adult standards, the most disreputable and unmentionable, and happens also to be a crime in English law.

https://www.cbeinternational.org/resource/cs-lewis-gender/

>CSL was undoubtedly alert to the huge changes going on around him, though he was no social historian and unprepared to learn from new fields of study. He found some illumination in the works of Freud and Jung, but notoriously resisted the arrival of sociology on the academic scene. In reading him, however, we need to be alert to the best of his shrewd insights into human behavior, “gendered” though much of these are. That is to say, his examples of women’s behavior are largely drawn from the domestic realm, and his examples of men’s from the non-domestic, as one might expect. But the value he places on domestic and family life for human wellbeing can hardly be underestimated, however much elements in it may need to be reconstrued.

In other words, Lewis was a complementarian, but one who actually believed in the spiritual equality of men and women, and the equal importance of women's roles on earth, even if he believed their earthly roles were different. Something that can't be said about a lot of complementarians, unfortunately, who use the idea of different roles to disguise their misogyny.

(as an side, im not a complementarian myself. i accept the arguments made by egalitarians who say that even if some complementarians are genuine, the structure itself allows for too much abuse and ought to be abandoned for that reason. but i still think it's valuable to distinguish between men who really believe in the importance of stay at home moms, and men who don't want to do chores.)

>A Grief Observed reflects these changes in CSL’s thinking and is devoid of “headship.” Looking back on the time he and Joy had together, he seems to have been able to rethink what he had said, because, although she was grievously ill, in her courage she gave to him at least as much as he gave to her, not to mention her love and care for Warnie as well as her two boys. So CSL wrote, “For we did learn and achieve something. There is, hidden or flaunted, a sword between the sexes till an entire marriage reconciles them. It is arrogance in us to call frankness, fairness and chivalry ‘masculine’ when we see them in a woman; it is arrogance in them, to describe a man’s sensitiveness or tact or tenderness as ‘feminine.’ But also what poor warped fragments of humanity most mere men and mere women must be to make the implications of that arrogance plausible. Marriage heals this. Jointly the two become fully human. ‘In the image of God created He them.’ Thus, by a paradox, this carnival of sexuality leads us out beyond our sexes.

None of these quotes, of course, would be enough to reconcile Lewis with modern feminism or gender rights. However, I think it is vitally important that when we make proclamations about a historical author's positions, that we place them in their own cultural context, and see which changes occurred over time as the author's own life played out (just as our own positions change over time). Lewis in particular had a lot of changes in his views on women after he was married to Joy.