Is it Yu or Yuu?

When I first arrived in Japan I could hardly pronounce names and words, let alone spell them! If someone wrote or spelled it one way, then that's the way I wrote or spelled it without question.

However things written in Romanji are a bit challenging to read. Mostly due to the fact that Japanese pronounce things differently and their alphabet has two letters per character, where as ours has one letter per character. For example: our alphabet it A B C D... and theirs is Ka, Ki, Ku, Ke, Ko... and so on and so forth.

After having studied a bit of Japanese and learned how spell things using Japanese characters, I have gotten an idea of how to translate things from Japanese characters to Romanji, but the challenge is that Romanji is for foreigners, so, do we write it the way a foreigner would pronounce it or the way a Japanese person would pronounce it (i.e. Katakana English or English English)?

Here are some examples, these are names I always question:

Yuu or Yu
Shouhei or Shohei
Soushi or Soshi
Ryouma or Ryoma or Rioma
Kyou or Kyo or Kio
Itoh or Ito
Oh or O

AHHH!! It drives me crazy. Usually it really wouldn't make much of a difference pronunciation wise, but when you are teaching a child to write their name in English for the very first time you want them to be able to learn to write it correctly. It would suck if after 5 years of writing your name "O", a teacher or the government would tell you you were wrong and that you should have been writing it "Oh".

Ah, the challenges of living in Japan! Simple, but frustrating!