So my brother and I have shared a gamertag for a LONG time, long as i can remember, and I want to get my own. Now, is there any way I can transfer my saves and DLC so they will work with another gamertag? I keep all of them on a USB for this reason. Yet, I went to test it out by trying to load them on my other brother's gamertag, and it didn't work.

Are character saves account bound? Or is there a way to get them to work on another gamertag that I create?

They are tied to that account.

Either you or your brother must start a new account, with a new gammertag and buy all the DLC's again.

Actually, this all sounds kind of fishy. Are you certain it's not just a cheep ploy to fish for illegal directions?

Eh? Illegal directions? No man, I just wanna play Skyrim on my own gamertag for once. I've invested hundreds of hours, like so many others, and I really don't want to abandon all of that. What is an "illegal direction?"