The Orange Box Question

It does come with a key for Steam. You will need Steam anyway. It cannot be played without Steam.

And whatever might be on those discs is probably out of date. You can chose to install it via the disc, but it would still require updates.

I don't know, why don't you just buy it on Steam? That's what I did, and I think it was well worth it.

as all of these games are clearly steamworks titles, they will activate on steam even if you but it retail. no disk is needed to play, but steam is.

Yes.

Yes.

I bought my Orange Box copy on a retail store back in december 2007.

The Orange Box retail comes with the CD Key for you to redeem the game on Steam and some installation DVDs for installing the games instead of having to download a crapload of stuff, it isn't needed to be inserted every time you want to play a game.

About the Team Fortress 2 Premium, I don't know for sure, but apparently it does. I'd wait to see some other responses about this one though.

Portal 2 came out with the code. I didn't even use the disc I bought from Amazon, I just redeemed the code.