Right now if my son has a separate gamertag on the same console he can share my DLC. What if he had his own separate account, could be still share?

Do you only have one Xbox?

Then yes.

Do you have two xboxes?

then maybe.


This is how I do it:
I buy the games and dlc on my account.
I make his xbox (which is at his mom's house) the primary xbox. So he can log in on his account and play all the games.
meanwhile, at my house, i log in on my xbox and i can play all the games.

This is how I got around having to buy two copies of everything.

for example:
I buy Halo on my account, install it on his xbox under my account, it's the home xbox, so any one that logs in to that xbox can play it.

meanwhile at home, i log in to my account and install the game there and i can play it anytime i want at the same time as him.