First, let me thank you for remaining civil. I've found conversing with you pleasant.

Bringing up that Shakespeare and Chaucer used the singular "they" is not justification for using it in the sense that you hid behind Orwell to justify your usage of "he".

In what way is it different? Both arguments rely on a famous author to determine the grammatical correctness of a certain construction. It is more precise to say that Shakespeare's usage proves that the usage of singular "they" is old. Indeed it is, and I don't doubt that at all.

I've found that a few people argue (and I paraphrase) "well, if the Bard used it, then there can't be anything wrong with using it in my writing". The argument is essentially "if it's good enough for Famous Author X, it's good enough for me" (I remember that somebody pulled this off when talking about Herman Melville, the author of Moby-Dick). In fact, I could argue that that argument might be more convincing to use with Orwell and other writers from the 20th century, since their English is more similar to ours than is Shakespeare's and Chaucer's. Thus, what Orwell found grammatical would match what we find grammatical more than what Shakespeare found grammatical does.

But I do not actually argue that generic "he" is correct because Orwell used it. I only supposed that if we were to use the works of famous writers to determine correctness of certain constructions in today's English (rather than check current usage), then there would be nothing wrong with my using Orwell, a much more recent author than Shakespeare. You can use the works of those authorities to prove that such constructions existed back in their time, but that in no way proves that they are correct today. The best way to determine that is by examining current usage. Current usage shows that singular "they" can't be considered "nonstandard".

Using Shakespeare to debunk "he" as the "official" gender neutral singular pronoun is a different story altogether.

I'm glad that you agree on that. To be clear, you do agree that both generic "he" and singular "they" can co-exist, even though one is much more used in common parlance than the other, do you not? Just because a famous author used "he" to convey gender-neutrality, it does not mean that "they" cannot be used for gender-neutrality for singular subjects, and vice versa. I'm fine with both options from a grammatical point of view.

"it's really my readers who prefer it" when it seems more likely you that prefers it.

Some background information of mine: I've been working on a fantasy novel, and right now, I intend to market it as a work that has a more "classical" style (the language is a little more literary and formal). It's a way to set my work apart from others (although this is by no means an original idea of mine). Interestingly enough, some readers view "he" as formal or dated, and singular "they" informal and more "modern" (others don't seem to notice either choice, and very few cared about it), so I thought that it might fit very well with my setting. Because of that, I inferred that the majority of my readers might think generic "he" more fitting for the setting of my work. That's what I meant by appealing to my readers.

In other words, my choice of using generic "he" in my writing is due to its being considered by some "dated" or "formal". If I have failed to state that in my earlier posts, then I apologize.

Personally, I find being precise but completely off the mark as being a waste of time.

Your personal preference is fine, and mine differs (I prefer to be "precise"). Of course, I can always use singular "they" should I want to do so. I use generic "he" as the main choice in my writing, but if I find that singular "they" works better (such as when the pronouns "everyone" or "no one" are used), I may choose to use them. Generally, I like to keep my options open.