Hold off on your DLC purchases for a day. I wish I had (spent 800 on Tuesday). Although with the RB2 import and some more DLC, I should still qualify.
there are conflicting reports on DOTW content. the previous link was from a XBox Social Media person in Europe. now Xbox Support says it SHOULD count. i would tend to agree w/Xbox Support on this one. regardless YMMV, just be aware until someone from Xbox officially clears this up.