Arrgh! Don't do this to me! It's like choosing the best uncle or grandfather!
They're scents of different natures, both are remarkable, but if I had to choose, Heritage would be a more wearable scent day to day. Habit Rouge has quite the personality, and if anyone considers getting HR, get the Legere version...it's now an oriental brought to modern standards. If you like the raw earthy animalistic nature of a frag, stick with the original.