Okay, so recently my house got a new Xbox. We transferred all the files and whatnot over to the new Xbox, and did the license transfer as well. However, it seems that Dawnguard is not showing up on my profile. Now, when we downloaded all the DLC for Skyrim, Dawnguard was downloaded on a roommate's profle. Hearthfire and Dragonborn were downloaded on mine. Oddly, Hearthfire and Dragonborn are working fine on my friend's profile, but Dawnguard is not showing up on mine. I tried deleting it and redownloading it, I also tried deleting it, clearing the cache and redownloading it, none of which have worked. I am at a loss here. Anyone have any suggestions here?

I'm not completely sure on this, but I thought you have to buy the DLCs for each player's profile. I have no idea why your roommate is able to play Hearthfire and Dragonborn, when he or she didn't buy them on his or her profile, unless your profile is being used by your roommate to play those two DLCs. Calling Xbox support may help you to solve this problem though.

No, we have always been able to play all the DLC that each other gets. The only time we have ever had trouble is now, when we got a new Xbox. Every other game that we have we have both been able to access all of the DLC, it is only Skyrim that we are having trouble with.

Sorry I wasn't able to of more help, but I did find a thread started by someone with a similar issue: http://www.gamesas.com/topic/1467967-dlcs-not-reading/

Maybe that will answer your question.

I have figured it out. It was quite simple really. I simply had to go on my friend's profile and do the license transfer from her account. I appreciate your effort though, thanks.