Nana: I will officially be using the abbreviation "DD" for Dumbledore from here until the end of time, thank you!
I think that DD felt honor bound by the legend of the Hallows to pass the cloak down to Harry. Even if Harry was NOT meant to be the one who brought all three together 6 years later, DD would have given it to him anyway. It was just how he worked, there are some kinds of magic that simply can not be ignored and the passing down of the cloak is one of those types. Harry was in aw when he realized that the cloak was his fathers. Touching the same fabric as his parents after never having met them must have been one of the best sensations of Harry's young life. In line with this gift of a connection with his parents, I like to believe that DD gave Harry the cloak in the hopes that he would explore the castle, like his father, and find the Mirror of Erised later in this same chapter. I think that DD timed this up for Harry, almost as an extension on his gift of the cloak. Just as DD hoped, Harry went exploring soon after Christmas and came across the Mirror where he was finally able to see his family for the first time. Dumbledore is the epitome of a loving person in this way.
I have always enjoyed reading about how Harry truly values the sweaters and food items he gets from Molly W. He has never had that display of love and appreciation from his true family and when he gets the ugly sweater for Christmas, he finally feels like, as Nana put it, part of the clan. So often we can take for granted the gifts we receive from friends and family for holidays, it has always been a part of our lives, for the most part. Fred and George joke about it, Ron rolls his eyes over it, but Harry throws the jumper on and smiles widely. Sure, a Firebolt, a homework planner, a broom compass, and a furry wallet with fangs are all nice gifts but I am certain that Harry values his inclusion a Weasley Family tradition above all others.
Alder with Unicorn hair, 14 1/2 inches, Brittle.
This is the comfort of friends, that though they may be said to die, yet their friendship and society are, in the best sense, ever present, because immortal.