ok here is how drm works
1 the gamertag that purchase it can use it offline or online on the original console and by all profiles
on any other console you can use it online only if the original gamertag is signed into live at all times.
however with a drm transfer to another console using the original purchasing any profile can use it on the new console offline or online this can only be done once a year
however the console that no longer has the license due to the transfer must have the original purchasing gamertag signed into live at all times to use the content.
its probably easier to buy it on a profile on the 2nd console so all profiles can use it on both consoles without the main gamertag being signed into live
what you can do for a demostration
sign into live on the 2nd console (before you do the drm transfer) with the purchasing gamertag
this will show you what i mean by being signed onto live it must remain connected to use it
but if you try it on the original console all profiles can use it online or offline