Trapped in the Chamber of Secrets for a day, having to flee the basilisk, surviving that I'd come out of it with character development.. as opposed to having my happy essence perma-stolen.
WYR have the Deathly Hallowed Wand or Invisibility Cloak (obviously no one should knowingly guard the stone)?
The Cloak. I could pretend that it's an ordinary invisibility cloak and "replace" it every so often. The wand is too conspicuous, and trackers could easily identify its ornate design and duel me to death to take ownership.
WYR: struggle with Devil's Snare or let Acromantula crawl all over you?