I don't usually post after 2 players, but Jax and my elbow (ref.: Status Update), gave me the occasion to do so. Here's a Like for you ( '-')b

So... Back to the (off-topic[.kek]) conversation.
As mentioned in my signature, I do translate things, but only as a hobby. More exactly, I do it either on a whim or I felt like doing it to broaden my mind upon finishing the work.
As much as I do take the lang' barrier issue seriously, and as I'd like to get a job around that, I'm just mostly afraid of the work environment I'll be in, should I find one. I wouldn't like it too stiff.

Anyway, the point of what I said.
The game wants Player 2 to state one thing they like about Player 1.

DJ Enetro wrote:

こちらの方の出身はハワイだから、彼が好きだ
(I like him because he is from Hawaii.)

What's after the comma makes the sentence tell that you like them, for this trait, instead of saying that you simply like this trait of theirs.
You're not wrong in the whole translation and the Jap' wording at all though. Just, wrong by a line invisible for some of us.
My version of the phrase, in order to tell the wanted latter, would be like this:

DJ Enetro Lv.+1 wrote:

こ{ちら}の方の出身地*(が/は)ハワイという所<ところ>が好き[です/だ]

{I put this part between this because the interlocutor would understand the subject either way}
*You might want to look into "出身", to see why I added 'chi' (地)
(I'm still hesitating between these two in such situation, but I'd go with the former)
<This word is pronounced 'tokoro', as written next>
[Both are correct too, but on a personal level, I'd use the former]

Doom, working on this message on the phone from 2:20AM to 3:45AM...
Drafts are really saving when you need to check some other things to prevent auto' refresh.

EDIT: I don't think I properly answered the question about my worrying.
In short, because there's a lot of "thin lines" to consider, especially hidden in the words we use, in whichever language.