It's an open secret that, for the past three weeks I've been mining the Featured Questions tab on SO as the basis of my reputation. It's been lots of fun (and really, isn't that the point, while asking great questions and writing great answers?), but I've noticed some worrying trends that, in my opinion, need attention to make this system work more effectively.
By category, ordered by my tersely-defined observed frequency, these issues are as follows:
Low-quality bounties by new or inexperienced users:
Simply: a bounty is unsatisfiable because a question's solution can't be determined without more information or psychic debugging. The common pattern here is users that build up just enough reputation to ask their first bounty, then take themselves down as close to 1 rep as possible. Not a problem per se, but a moderation view and common resolution for this scenario (as "not a question") would be nice.
Off-topic questions and violations of site policy:
Bounties where an inappropriate question escaped being closed on its inception or where it immediately is promoted to bounty status by the OP before mods have a chance to act (that is, mods failed to give it the attention it needed before it became eligible for a bounty). In these cases, votes to close are disabled for the bounty duration. These aren't always a problem (they're easy to identify and flag for ♦ diamond moderation), but they're irritating in their frequency and inconvenience in closure.
Fire and Forget:
Simply, cases where the bounty provider asked their question and abandoned it. This is very common in the +50 range, which is why I'm averse to answering at that level unless doing so has wide applicability (garnering a minimum of +2 for policy-bound reasons). I think an extended FAQ might help, here.
Bait and Switch:
Sparsely common, but very insidious. These are cases where the parameters of the bounty have been satisfied and, just to get that extra mile out of Featured status, a litany of follow-up questions is asked before the face value is granted to an answerer. I generally take these as given (and as helping the user; rolling to chat is common), but some level of policy should ideally be draped around this scenario, because of its commonality.
I believe these issues haven't yet been addressed because, for the most part, the difficulty is on the other end: getting people to place bounties on questions at all. Furthermore, I believe the perception is that a seven day bounty period is seen as a reasonable protected window before re-enabling closures except in extreme circumstances. I empathize. I think, however, that there should be a precondition of following the site's rules (especially regarding off-topicness) to keep some subset of these bounties rolling.
My current recourse, because bounty placement disables the ability to vote to close a question and other moderation options do not exist, is to flag the question for diamond moderator review. I think, however, that this is inelegant and the issues are reproducible enough that we can bring some of this moderation down to the 10k consensus level.
I have my own opinions of how to resolve these scenarios, but I'm curious of how, as a matter of policy, you'd resolve these as a theoretical member of Fog Creek. Because that's the joy of Meta: we can speculate and deliberate while Jeff
^W Joel and company work on giving us the tools we need.
Remember, the goal is we want people to answer these, not just a few schmoes like me that worked out a system to navigate minefield and tar pit questions. Anything we can do to make moderation of these questions easier, to keep them as helpful and useful as possible for all involved, is worthwhile here.