Thanks, that’s helpful. I also suspect that there’s a similar principle behind both phrases, but I’m curious now: How do you personally see で?
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Hm… as the て-form of だ above all, with most functions being derived from that? Or as a mix between that and a ‘means’ particle. In the case of 君は君でいいよ, I’d say either meaning works. You are good just being you, or you are good even if the basis of your lifestyle and existence is you. For その時はその時で, I guess the て-form interpretation is good if you want to focus on ‘that time being that time’ and not being presently relevant, or being different from some other time. Can we use the ‘means’ particle interpretation? Well, maybe this is technically an incorrect or imprecise interpretation, but it seems like it’s also explained by some sites as meaning ‘when that time comes’, and it certainly seems to be used that way by some people, so you could say it’s kinda like how some people explain the existence of 後で: one uses ‘that [point in] time’ to consider the issue. I think the て-form interpretation is more appropriate in this case, but I think both work.
That’s basically it. Fun fact: apparently で is actually descended from に+て in Classical Japanese, but because I haven’t had enough time to study the details of Classical Japanese grammar, I’m not sure how to interpret that, especially because に might be the particle or one of the forms of the old copula なり (basically the classical version of だ・である). I guess we can just treat that as a bit of trivia for now. Hahaha.
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That’s interesting. I always secretly thought that the particle で might have been the て-form of だ originally, because in several cases (like the one we’re discussing) it seems to me that either of them would work. Not so, apparently 
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Oh, it might be, actually, at least indirectly, because に as a verb form is essentially the equivalent of… であり? It’s the masu-stem of なり. (‘Masu-stem’ isn’t the right technical term, especially since I don’t think にます actually existed at any point, but Japanese uses the same word – 連用形 – for the thing that acts as the masu-stem.) If you know that the て-form is historically just the masu-stem + て followed by sound changes, well… that means that にて is essentially the て-form of the equivalent of だ・である。
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Question about these sentences I made. Are either of them correct? And if so, which one sounds more natural?
私は鳥如しに寝ました。
鳥みたいに寝ました。
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I think in the first sentence you’d use 如く rather than 如しに. 如し is an auxiliary verb, not a noun, and is essentially analogous to (の)ようだ, with 如き and 如くbeing conjugations of it analogous to (の)ような and (の)ように/で respectively, hence 如く being the appropriate form to use.
I feel like みたい is more natural, but also a lot more casual. I also recall there being some nuance of the similarity expressed by みたい being visual, or at least bearing some visual/visible characteristics, but I’m not quite sure whether that’s the case, and it doesn’t always seem to fit. Depending on what you’re trying to express though, there might be a better fit (I’m not sure what you mean by sleeping like a bird).
From what I gather 如し/如き/如く isn’t really used anymore, it’s a bit archaic and has almost entirely been replaced by some variation of よう depending on which you use. So instead, 鳥のように寝ました might be more natural/less archaic, and still somewhat formal.
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Also, besides the fact that 如し should be 如く when used as an adverb, from what I can tell it should be 鳥の如く, just like you’d say 鳥のように.
I’ve always found the “auxiliary verb” term funny since it’s not really used as a verb. But that’s how 助動詞 is often translated anyway.
But yeah, 如し and its various forms is easy to keep track of when you know classical 形容詞 conjugations since they are identical.
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Even more casual would’ve been 鳥っぽい, but I agree 鳥のように寝ました。 sounds the most common and natural.
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っぽい might actually be so casual it feels out of place in a sentence ending in 〜ました 
Not sure about that though.
EDIT: Actually, searching for っぽいです does give results, so maybe it can be used in polite sentences just fine.
But doesn’t that also carry a different connotation than みたい or のように? I can’t quite explain it, but it has a different “feel” to me, maybe closer to らしい than to みたい in describing some kind of “inherent” characteristic, so something like 女性っぽい feels to me more like “feminine” than “resembling a girl” whereas 女性みたい is more “resembling a girl” than “feminine” (you know, aside from the considerable overlap between those). Does that track with your interpretation of it?
Ah, it was my understanding that 如し does in fact take the place of a predicate or verb, but I’ll admit I basically learned about it on the spot so there’s a good chance I misunderstood something here or there
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Yes, definitely. I wouldn’t say they mean the same thing, but ultimately it depends on what wants to say. The っぽい was just a low ball from me, sorry 
Regarding みたい I’ve seen it more at the end of a sentence clause in a similar way らしい is used in that position and sometimes らしい after nouns (as you said, emphasizing “Y having the features of X” in a XらしいY sentence), but みたい not as often. I’ve seen のような or のように way more often in general.
For “feminine” I think I would rather use 女性的.
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I think technically a 助動詞 is anything that goes at the end of a word (sometimes after that prior word has been conjugated) and can itself be conjugated. For example, たい as in 行きたい is also a 助動詞 even though たい is clearly not a verb in the traditional sense.
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I mean, relative to how we learn grammar and how things are designated in Japanese, 如き behaves like one of the Classical Japanese ancestors of い-adjectives today, and those are just 形容詞, which we usually translate as ‘adjectives’. But 如き usually can’t function alone, so it’s an auxiliary word, and its classification in Japanese is indeed 助動詞. Even ない is technically a 助動詞.
It seems like it works with or without the の. I think I’ve seen the version with の more often though.
Based on dictionary definitions, っぽい (which should be transformed into っぽく in this case so it can act as an adverb) is more about showing a certain tendency or very much giving a certain feeling. みたい, at least in this usage, is more about resembling something in general appearance or shape.
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The serendipity of Duolingo:
学生っぽく見えるけど、彼は会社の社長なんです。 
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For the Aしか~ない grammar point, can A be an adverb?
For example, would it be wrong if I said something like 漢字は醜くしか書けない?
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Yes. From 大辞林:
(I didn’t bother copying the definition/meaning explanation because I think most people would have come across it shortly after starting to study Japanese grammar. Also, I swapped an active form for a passive form, and translated technical terms with their most intuitive equivalents, not conventional technical equivalents in English, so sorry if anyone feels I’ve been imprecise.)
You can basically attach it to any of the usual parts of speech in Japanese, as long as you use the right form.
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Great, thanks!
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In this sentence, is であろう supposed to indicate conjecture?
掌の上で少し落ちついて書生の顔を見たのがいわゆる人間というものの
Seems like it to me. であろう is basically だろう, except it’s from である instead of from だ.
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Okay, that seems to make sense. I’ve also seen other verbs conjugated with ろう besides である, but I think it might mean the same thing.
例文
もし私の好奇心が幾分でも先生の心に向かって、研究的に働き掛けたなら、二人の間を
大辞林
たろ◦う
（連語）
〔過去の助動詞「た」の未然形に推量の助動詞「う」の付いたもの〕
活用語の連用形に接続する。ガ・ナ・バ・マ行五（四）段活用の動詞に付く場合には「だろう」となる。
①過去の事柄やすでに完了し実現した事柄についての推量・想像などの意を表す。「その時は，さぞ困っ━◦うね」「あの人の口から出たんじゃなかったら，僕も頭から信用しなかっ━◦う」
②（多く上昇調のイントネーションを伴って）過去の事柄やすでに完了し実現した事柄について，相手に念を押したり同意を求めたりする気持ちを表す。「お父さんもまだ小さかっ━◦う。ちょっと怖かったよ」「この間話し━◦う，そんなことは考えない方がいいよ」Is there any difference between “の心配している” & "を心配している?