I know there isn't a particularly distinct difference between L and R in
native Japanese, but very often proper nouns and other non-translated Japanese
names/words work their way into English translations. An odd thing I've
noticed is that often when media is re-retranslated, Ls and Rs get flipped in
proper nouns.

I've noticed this a lot in Final Fantasy games in particular (Rally-ho turned
into Lali-ho), and generally the later translations had better English.
However I haven't really noticed more Ls turning into Rs or vice versa; I
haven't seen any particular pattern to the changes at all, so I'm wondering
what (if any) logic is behind it.

Is there a "proper" way of determining whether a sound should be
transliterated as an L or an R or are L and R picked simply based on which
"sounds better" to whoever is doing the transliterating?
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rōmaji
How is determined whether a sound should be romanized into an L versus an R?
> Are L and R picked simply based on which "sounds better" to whoever is doing
> the transliterating?

Sometimes it's this, and other times it's about figuring out which is correct.

It extends to more than just "L" and "R", by the way. For instance:

  * ロック・リー ( _rokku rii_ ) (from Naruto) : Rock **Lee**
  * ジュリー ( _jurii_ ) : Ju **lie** ... or ju **ry**
  * ジェリー ( _jerii_ ) : Je **lly** ... or, Je **rry** ... or, **Ge** rry...

The only way to decide is through context and educated guesses about what the
author had in mind (or asking them). Working it out can be particularly
difficult for names or newly coined terms, and even more so (for English
speakers) if additionally the language it seems to be pulled from is some
other language like German or Spanish.

A novel I'm currently reading has the character name ルルウ ( _ruruu_ ). The
other character names are エラリイ ( _erarii_ ), アガサ ( _agasa_ ), ポウ ( _pou_ ),
and so on.

Therefore, it is possible to deduce (although in this case the novel tells
you) that these are references to famous detective fiction authors (Gaston
**Leroux** , **Ellery** Queen, **Agatha** Christie, Edgar Allan **Poe** ), and
so those would be the appropriate translations. Sometimes, this level of
research is required to produce a good translation (unless you can ask the
author), and translators who miss cues like these, or fail to research them,
will result in "flipped L/Rs" and various other things.

In other cases, the original author may not have a specific transcription or
reference in mind, and then it would seem to be up to the personal preference
of the translator.
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I'll talk about the case for made-up words(造語).

The tendency is that translators often romanize any ラ行(r-line) sound into R as
a temporary measure simply because ラ行 sounds are shown as Ra Ri Ru Re Ro. That
is because whether a ラ行 sound has to be written in L or R when romanized is
something only the creator of the word would know.

Take your R(L)ali-ho example, whether "ラ" in ラリホー is intended to be written in
L or R is something only the creators of Dragon Quest would know. You have to
ask the creators directly or play the translated version of the game to know
the proper spelling when it comes to words like ラリホー which does not give you a
clear clue as to what language the creators want it to sound like.

In some cases, as Hyperworm mentioned, the creator does not even have a
specific transcription in mind, in which case, the only thing that matters is
the personal preference.

*edit:For some reason, I thought ラリホー was a spell from Final Fantasy by mistake. I don't know why I thought that and fixed.
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