Just for the future, if I were to upgrade to the One, would I have to buy The Taken King bundle (either digitally or a hard copy) again plus Rise of Iron if I already have TTK digital copy on my 360? I have Destiny saved on a hard drive that I believe is transferrable between the Xbox One and the 360, so I couldn't I just pop the drive into the One and start playing? Thanks for the help in advance.
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No it is not transferable. You have to re-buy everything, however the Destiny: The collection upgrade is just for people like you that are upgrading. It is only $10 more than rise of iron by itself and includes everything.