Can I gift games to people in other areas of the world?
On my Steam account, I have a copy of The Orange Box I gifted to a friend during the Christmas sale. He is not interested in the games Orange Box has that he doesn't already have.
Is it possible for me to resend this gift this to someone in another region?
This is a two-part answer.
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Yes, you can gift items to people who live in other areas of the world, so long as the gift hasn't been redeemed yet. For example, I live in Europe, but I have received several gifts from friends in the US.
See also Left For Dead 2 - Unlock Australian Censorship about how region restrictions carry over in gifts.
If you gift the Orange Box to someone, there is only one key, which unlocks all 3 games in the Orange Box Collection. You cannot gift these games separately, unless your friend already owned a copy of Half Life 2, in which case he will receive an extra gift copy of Half Life 2, which he can then give to someone else. However, this is a rare case. If your friend has already registered the key with Steam, it cannot be used again.
Source: Steam's Support Site regarding Extra Copies
Provided your friend has not redeemed the gift, you can resend it to any email address you so desire. In fact, Steam recommends gifting a game to yourself if you would like to give it away on a later date, as all the other user requires is the unique key. However, once a game has been redeemed, it is permanent.
Source: https://support.steampowered.com/kb_article.php?p_faqid=549
As for the region, they will receive the version of the game from which it was purchased. In the case of L4D2, the recipient will receive the non-censored version if they are Australian but the purchaser lives in the US. There are no restrictions in sending gifts across regions.
Source: Experience gifting 32 games on Steam, including two L4D2 copies for Australians.