Orange Box (Question)

You'll probably get gift copies
I'm not sure though

Nope, you will get the games you don't have. You won't get giftable copies of the ones oyou already have. Personally I had the same problem with Condition Zero and didn't enter any giveaway containing it unless it was the individual title. Later on a member of this comunity offered me a pack with Counter Strike + Condition Zero and even though I already had CS I didnt get it as a giftable copy.

just make a new account and activate on it?

I do believe certain games will give you a giftable copy (i don't know which ones). However, your probably just going to get the games you dont have.

If you are asking about what will happen if you enter for the giveaway on this site? I do believe it will recognize if you have the orange box already and not let you enter even if you tried. Go ahead and enter the giveaway for it. Might make the gifter mad that your wasting part of it but not against the rules. If you have most of the games, the nice thing to do would be not enter and let someone who can make the most of it win.

The only games that become giftable are Cogs and some Valve game (like the Half-Life serie)

How come some of the answers here are completely wrong to half right/wrong?

There are only a couple of games that you get a second gift copy for if you buy a pack containing those games; the Half-Life 2 games are some of those games, so you would be able to buy or be gifted the Orange Box while already owning Half-Life 2 and get a free copy. As for TF2, did you actually purchase it or is it the free version? Because if you only have it because it's free you would be upgraded to a Premium Account. If you already have a Premium Account I don't believe you get an extra copy of it but given its free status I don't think it's a large issue.

When you redeem an Orange Box, you only will receive extra copies for HL2 and HL2:EP1, at least that happens with the retail Orange Box, i'm not sure if with the digital copy happens the matter.

Yes, you will recieve giftable copies of same games in the pack. Tested.