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The following is the procedure needed in order to win the coveted Maverick hat during Winter Bash 2016/17

  1. Find a question that is scored -3.
  2. Answer it.
  3. Wait until your answer is scored +5 and the question is scored +3.
  4. HAT!

source

What happens in a bounty scenario? Let's say the OP was -4, then it received an answer, the question was upvoted but it still didn't reach that all-important +3. Lets say the "new" answer is stuck at +3, it needs two upvotes to stand any chance of earning the Maverick hat.

  • What if the same user placed a bounty on the question, can they still earn the Maverick Hat if the requirements are met? Does placing a bounty violate the rules?

What happens if someone else posts an answer during the bounty, and this answer receives 5 upvotes?

  • Although they posted an answer when the question had more upvotes than downvotes, does their +5 answer (posted during the bounty period) mean they receive the Maverick hat?

ADDED
I don't want to ask a new question but it is related to the above. If I were to place a bounty on January 2nd, the user who is awarded the bounty on January 8 should get me the Philantropist hat. Right?

3

The description says nothing about bounties.

Since the source you gave also never mentioned any special cases, we can fairly assume that regardless of bounties are put on the question or not, as long you:

answer +5 a -3 question that goes to +3

regardless if the answer was the first or not. Of course, the question must reach a score of 3 before the hat can be awarded.

What if the same user placed a bounty on the question, can they still earn the Maverick Hat if the requirements are met? Does placing a bounty violate the rules?

Fair play to me. animuson never added anything about bounties violating the rules so it's practically fair play.

Although they posted an answer when the question had more upvotes than downvotes, does their +5 answer (posted during the bounty period) mean they receive the Maverick hat?

If the question at the time of posting this answer wasn't at -3 or below for its score, regardless of the answer's score, the OP of the answer would not receive the hat. It literally says in your source:

Find a question that is scored -3.

Emphasis mine. So if it started at -3 but was like +2 when you answered, your answer is void for the hat.

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