One of the SE features I like is the notion of privileges:
Privileges control what you can do on Mathematics Educators Stack Exchange. Gain more privileges by increasing your reputation (points you receive from your fellow users for posting helpful questions and answers) https://matheducators.stackexchange.com/help/privileges
For example, if you have 500 points, then you can cast close/reopen votes. To me this is a nontrivial privilege, and one that should be earned by asking/answering good questions. 500 points means 50 up-votes on your answers or 100 up-votes on your questions or some combination of the two.
However, there is also a bounty system on SE (another feature that I like, in general) in which a user can put out a bounty of up to 500 points on a single question.
More precisely, one user can use the bounty system to bestow the privilege of casting close/reopen votes on another based upon a single response. For a recently opened site like MESE, it also gives the impression that the bounty-recipient has some high level of expertise: 500 points alone would put someone at the top of page two of user reputation at the time of this posting.
Many details are omitted here, and I can see many possible lines of argument with regard to offering bounties, but here is my question: Should those offering a bounty be expected to try it first with a reasonably small number of reputation points (e.g., 50 or 100) or is it fine just to go for the max (500)?
For a more general question: What are some factors to consider when designating a bounty size?
(Please note that this meta post is motivated by the current question with a 500 point bounty, but not explicitly directed at that question. I am asking about the situation more generally.)