steam
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?
Any games you receive additional copies of will appear in your Steam Inventory. You can access your Steam Inventory by clicking on the View menu followed by Inventory, or clicking on the 'envelope' on the Steam titlebar;
This will bring up your Steam inventory;
From here you can select any item and send it to a friend, either by using their Steam account name or email address.
There is no option to send money to the wallet of your friend directly.
What you can do however, is buy a Steam gift card at GameStop and send that code to your buddy so he can activate it. I do not know if that works cross countries though. But if you both live in the same country and GameStop has those gift cards available, then it would be no problem to activate it.
Another option would be to put an TF2 item on the Steam Market and you buy that. Valve takes a cut here though, so it is not really viable and I don't recommend it.
The best option imho would be just to ask him what game he wants and gift that directly.
Best Answer
This is a two-part answer.
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