Transferring Xbox Live to another user

Once a code is redeemed on an account, there is no recovering it or transferring it.

On top of all that I described before, I have 2 Windows licenses under my primary account. If MS would just be able to transfer all that to another account, then I see how it would work. Otherwise I am stuck.

It's not an option and probably won't be any time soon, the potential for abuse is just too high. But I empathize with your situation, that's a hassle for you.

Actually yes the 360 did have this capability. At one time you could transfer the rights and permissions to another user. I don't remember if it had to be some one in your family or just some other user on that counsel. I have used it multiple times to
transfer the rights and permissions when I first started playing on the system. It was the way to purchase the content through my account and transfer the rights and permissions to my son

Your son might just have to deal with losing all his progress then, I can see why you don't want to create a new account for your self, and that's totally fair.

You can always head over to
Xbox Ideas and put your idea forward.