Need Help ( Downloads New 360 )

[sega4life]

Ok so I got my Son a 360 for his room..

I got his gamertag on his own 360 but I have a question..

over the years we downloaded stuff on both our accounts, like games and DLC some went under my name, some under his..

so the games /DLC that are under my name he can no longer get on his 360 right?

Is there a chance I call Xbox and tell them I would like my Son to have the same DLC as mine, so I do not have to pay twice?

I don't really want to pay for two sets of everything like games and DLC..

Also I still have his name in my 360, if I connect online using his name by mistake, and he's online in his room, will that cause some kind of problem?

Also #2 if I transfer my gamertag to his 360 and redownload all the DLC to it, but he never signs under my name will that work?  ( I think it will )