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We know that Yamada is not afraid of anything. Then, Nagasawa says:

「山田君のように、怖いもの知らずっていうのにも、ちょっと憧れちゃうけどな...」
Like Yamada, even though I said I'm not afraid of anything, I have a little admiration but...

I think my translation must be wrong because Nagasawa never did say that he wasn't afraid of anything (we only know this about Yamada). Also, It's not clear to me why this would result in him having admiration.

So I think I'm messing up the っていうのにも part. I'm guessing that the whole sentence is supposed to mean:

I have a little admiration for people like Yamada who aren't afraid of anything but...

But I can't bend っていうのにも to my will. How do I break down this sentence?

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「[山田君]{やまだくん}のように、[怖]{こわ}いもの[知]{し}らずっていうのにも、ちょっと[憧]{あこが}れちゃうけどな...」

「っていうのにも」=「っていうの + にも」

「の」 is a nominalizer. ⇒ "this thing called 怖いもの知らず (as seen in Yamada)"

「に」 always goes with the verb 「憧れる」 as in 「~~憧れる」 = "(I) yearn for ~~", "(I) long for ~~", etc.

「も」 here is the implicit kind of "also" and I am sure you have seen it before (because we use it like 80 times a day, literally). The speaker does not say what other things he longs for.

Thus, the middle part of your first TL: "Like Yamada, even though I said I'm not afraid of anything, I have a little admiration but..." is pretty much guesslation. The speaker did not say anything, and it is not him who is not afraid. It is Yamada.

Your second TL is much better and is closer to what the original says.

My own attempt:

"I sorta yearn a bit for the (kind/level of) fearlessness as Yamada's, but..."

2

There are a few things that aren't literal here.

っていう

This can mean "that kind of thing", "the fact that", etc. It does not mean that anyone has actually said anything about it. In this case, 怖いもの知らずっていう would mean something like "The thing known as not knowing fear".

けどな...

This may actually mean 'but' depending on the context, but the rest of the sentence makes it sound like a casual 'though' that doesn't link up to anything. For example, "I already went to the supermarket though", "I still want cheese though", etc.

As for のにも:

「の」is basically the same as 「こと」in this case. It's kind of hard to translate into English, but you've probably seen this construct in something like 泳ぐが好き for example.

「に」as another answer said is related to the verb 憧れる.

「も」is used in the sense that "This isn't bad either".

So the closest translation would probably be:

"I also kind of yearn to be fearlessness like Yamada, though."

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I have a little admiration for people like Yamada who aren't afraid of anything but...

You've got the gist.

Anecdotally, if someone actually said something, the Kanji 「言」 is used in 「~と言う」. If no Kanji, then you're bringing the preceding statement into the spotlight. Here, it can be interpreted roughly as "the fact that", but its real use is more general. という, っていう, or just って are used like this:

[猫]{ねこ}って[動物]{どうぶつ}は[可愛い]{かわいい}な

お前っていうやつは・・・ (common in Anime/Manga)

君は何でもできるというのがすごい

If you get the last example, you should be able to retackle your sentence.

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