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I don't know if the answer depends on the system used. Information on this is
welcome too, but mainly I'm interested in the Hepburn system.

When romanizing a kanji compound, how do you decide if you should use a space
or not? For example, should 女教師 be "Onnakyoushi" or "Onna Kyoushi"? Should
生徒会長 be "Seitokaichou" or "Seito Kaichou" or perhaps even "Seitokai Chou"?
What about 沖縄開発庁長官, 銀河鉄道, 銀魂, 修学旅行?

Is there even a correct\established method, or is it just a matter of
preference and there are no right or wrong answers?
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2016-03-09T19:12:11.593
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2016-03-10T00:52:49.643
2016-03-09T19:42:22.267
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rōmaji
Romanization of kanji compounds: when are spaces used?
Romanization conventions are a bit fuzzy. Generally speaking, the practice
I've seen is to group the romaji based on the breakdown of a longer kanji
string into singles or two- or three-kanji compounds, based on the underlying
semantics. Some folks might use hyphens to clarify three-kanji compounds.

To use your examples, I might romanize like:

  * 女教師: 女{おんな} here is clearly an independent lexeme, as indicated also by its reading -- _onna_ is _kun'yomi_ , while _kyōshi_ is _on'yomi_.  
→ _onna kyōshi_

  * 生徒会長: This is 生徒会{せいとかい} + 長{ちょう}, as in the head (長) of the student's (生徒) association (会) → I've seen various renderings of this kind of structure; subjectively, I think the last one is the least user-friendly.  
→ _seitokai chō_ , _seitokai-chō_ , or _seitokaichō_

  * 沖縄開発庁長官: This is composed of three lexemes: 沖縄{おきなわ} + 開発庁{かいはつちょう} + 長官{ちょうかん}. The middle one itself is 開発{かいはつ} + 庁{ちょう}, which could be hyphenated.  
→ _Okinawa Kaihatsu-chō Chōkan_ , or _Okinawa Kaihatsuchō Chōkan_

  * 銀河鉄道: Two lexemes: 銀河{ぎんが} + 鉄道{てつどう}.  
→ _Ginga Tetsudō_

  * 銀魂: This could be parsed either as two lexemes, 銀{ぎん} ( _on'yomi_ ) + 魂{たま} ( _kun'yomi_ ), or as a single name, 銀魂{ぎんたま}.  
→ _Gin Tama_ , or _Gintama_

  * 修学旅行: Two lexemes, as 修学{しゅうがく} + 旅行{りょこう}.  
→ _shūgaku ryokō_

All that said, if you're looking to romanize the name of an organization or
job title (such as the 沖縄開発庁長官), google around a bit -- there might already be
an official romanization in use.
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