Did Dumbledore plan to have Harry possess all 3 Hallows?

Question

Did Dumbledore plan to have Harry possess all 3 Hallows?

Answer 1

No, Dumbledore never possesed all the three Deathly Hallows at any point of time.

He only came into possession of the Resurrection Stone after Year 5 (when he found it in Gaunt's shack) and he has not had possession of the cloak in the year 6 at anytime before his death. He did possess two of them at a time (wand and cloak between Harry's birth and Year 2; and wand and stone during Year 6).

The only person who (as far as we know from canon) came close to possessing the three Deathly Hallows at the same time is Harry Potter:

• He physically possessed them close to each other (he dropped the Resurrection Stone in the Forest very shortly - probably less than 1/2 hour - before obtaining physical possession of Deathstick after Voldemort died).

• Also, while he had that 1/2 hour gap, he was indeed the true owner of Deathstick all that time despite not physically holding it - ever since he disarmed Draco Malfoy.

• Dumbledore acknowledged Harry as the "Master of Death", meaning the true owner of all 3 Hallows, in King's Cross:

  If you laid hands on them, I wanted you to possess them safely. You are the true master of death, because the true master does not seek to run away from Death. He accepts that he must die, and understands that there are far, far worse things in the living world than dying.”

---

As far as "planned to pass them on to Harry" had he possessed them, he did not (only planned for 2 out of 3) when he was alive, but he fully acknowledged his error and reverted his judgement during the conversation in King's Cross chapter of Deathly Hallows (all the quotes from there).

• He acknowledged that Harry was the rightful owner of the cloak.

  “The Cloak, as you know now, traveled down through the ages, father to son, mother to daughter, right down to Ignotus’s last living descendant, who was born, as Ignotus was, in the village of Godric’s Hollow.”
  Dumbledore smiled at Harry.
  “Me?”
  “You.

  ...

  “But the Cloak, I took out of vain curiousity, and so it could never have worked for me as it works for you, its true owners

• He was afraid that Harry might be tempted by the stone (though he later realized he was wrong and gave the stone to Harry in his will - but did make it hard for Harry to learn it was a Hallow):

  “Real, and dangerous, and a lure for fools,” said Dumbledore. “And I was such a fool. But you know, don’t you? I have no secrets from you anymore. You know.”

  ...

  “Can you forgive me?” he said. “Can you forgive me for not trusting you? For not telling you? Harry, I only feared that you would fail as I had failed. I only dreaded that you would make my mistakes. I crave your pardon, Harry. I have known, for some time now, that you are the better man.”
  “What are you talking about?” asked Harry, startled by Dumbledore’s tone, by the sudden tears in his eyes.
  “The Hallows, the Hallows,” murmured Dumbledore. “A desperate man’s dream!”

  ...

  “I am afraid I counted on Miss Granger to slow you up, Harry. I was afraid that your hot head might dominate your good heart. I was scared that, if presented outright with the facts about those tempting objects, you might seize the Hallows as I did, at the wrong time, for the wrong reasons. If you laid hands on them, I wanted you to possess them safely.

• He never planned to give Harry the wand – his original plan was to die with the wand physically buried with him and Severus its owner:

  “If you planned your death with Snape, you meant him to end up with the Elder Wand, didn’t you?”
  “I admit that was my intention,” said Dumbledore, “but it did not work as I intended, did it?”

  ...

  “Aren’t you listening? Snape never beat Dumbledore! Dumbledore’s death was planned between them! Dumbledore intended to die, undefeated, the wand’s last true master! If all had gone as planned, the wand’s power would have died with him, because it had never been won from him!”