I feel like I should provide some data as someone who participated in a number of past bounties.
I don't think it's possible on LW. It's not a matter of money (ok, it is, in that I don't think anyone's likely to offer a compelling bounty that I expect to be able to win). It's not a matter of reliability of available offers (except that I don't expect ANY).
It's _is_ a question of reliability and trust, though. There are no organizations or people I trust enough to define a task well and make sure multiple aren't competing in some non-transparent way, so that I actually expect to get paid for the work posted on a discussion site. And I don't expect that I have enough track record for any bidder to prefer me for the kind of tasks you're talking about at the rates I expect. [edit to add] Nor do I have any tasks where I'd prefer a bounty or open-bid rather than finding a partner/employee and agreeing on specific terms.
It's also a question of what LW is for - posting and discussion of thought-provoking, well-researched, interestingly-modeled, and/or fun ideas is something that's very hard to measure in order to reward monetarily. Also, I'll be massively demotivated by thinking of this as a commercial site, even if I'm only in the free area.
My recommendation would be to use a different place to manage the tasks and the bid/ask process, and the acceptance of work and payment. Some tasks and their outputs might be appropriate to link here, but not the job management.
tl;dr: don't mix money into LW. Social and intellectual rewards are working pretty well, and putting commerce into it could well kill it.
If answering the question takes weeks or months of work, won't the question have fallen off the frontpage by the time the research is done?
What motivates me is making an impact and getting quality feedback on my thinking. These both scale with the number of readers. If no one will read my answer, I'm not feeling very motivated.
For the examples you give, the improvements you cite to intrinsic motivation + karma would be sufficient to motivate me for questions of the "take an afternoon of your time" type, which is approximately where my blogposts have been landing anyway. Further, several are already of the summarize papers/point to a list of sources type. On the long end of weeks or months, bounties in the hundreds would probably satisfy depending on the level of interest I have, which is the true variable in whether I engage.
It is hard to tell in the current format what kind of depth-of-answer the questioner is looking for, and what time frame would be appropriate for an answer. It is also hard to tell how well answered a question already is, which has a big impact on reading older questions or questions with many answers. Mostly I have been viewing questions at the same rate as blog posts, but it occurs to me that they don't age in the same way informative or exploratory posts do; the question is unresolved until it is.
Having some way to disentangle the content of this site from when it was posted would be handy.
It would help if the poster directly approaches or tags me as a relevant expert.
Given that there is some probability of winning a question, let's just guess it's 20% on any particular question I might try to answer. This suggests to me a bounty of 5x whatever I would be willing to answer the question for in order to make me willing to do it. Assuming a question takes about a day of work (8 hours) to answer fully and successfully, and given our 5x multiplier, I'd be willing to try to answer a question I wasn't already excited to answer for other reasons if it paid about $1800.
Many others may have lower opportunity costs, though (and I undercounted a bit because I assume any question I would answer would deliver me at least some sense of value beyond the money; otherwise my number would probably jump up closer to $2500).
In order to be motivated, I would like to have a good idea of the impact the work would be making. I would like to see a clear explanation of the process taken to come up with the question and a list of who in LW supports this question as being an effective target of attention at this point in time and why. Maybe this could be documented in the question post and maybe there could be rounds that potential questions to go through for community members to vote/discuss/rate them. Maybe there could be a backlog of other questions that have not been chosen yet with reasons why they have not been chosen yet to help new questions arise. I would also like to know which other LW users are working on it (to avoid duplication of efforts) and if there are good opportunities for delegating work among multiple community members.
I like the idea of sub-questions. It might be interesting to have a display in the form of a graph with vertices as question/answers and directed edges as indicating a sub-super relationship between questions/answers. I think this would help us get a big picture view of the progress made and how it was achieved.
Since there is only so much that can be done by one community, I think it could in some cases be useful to have questions that are intended to be handed off to external parties like academic groups or certain organizations or renowned individuals after we do enough investigatory work.
If this blog's "hard questions" have utility, they should be novel, important, and answerable.
Important questions are highly likely to be known already among experts in the relevant field. If they're answerable, one of those experts is likely already working on it with more rigor than you're capable of extracting from a crowd of anonymous bloggers. I think, then, that any questions you ask have a high probability of being redundant, unimportant, or unanswerable (at least to a useful degree of rigor). Unfortunately, you're unlikely to know that in advance unless you vet the questions with experts in the relevant literature.
And at that point, you're starting to look like an unaccountable, opaque, disorganized, and underresourced anonymously peer-reviewed journal.
It might be interesting to explore the possibility that a wiki-written or amateur-sourced peer reviewed journal could have some utility, especially if it focused on a topic that is not so dependent on the expensive and often opaque process of gathering empirical data. I expect that anyone who can advance the field of mathematics is probably already a PhD mathematician. So philosophy, decision theory, something like that?
Developing a process to help an anonymous crowd of blog enthusiasts turn their labor into a respectable product would be useful and motivating. I would start by making your next "hard question" what specific topic such a PRJ could usefully focus on.
One of the questions (ha) that we are asking ourselves on the LW team is "can the questions feature be bootstrapped into a scalable way of making intellectual progress."
We'd like to make it easier to attach bounties to questions, and to make it easier to break questions into smaller, easier chunks.
What would it take for you (you, personally), to start treating "answer LW questions" as a thing you do semi-regularly, for money?
My assumptions (possibly incorrect) here are that you need a few things:
Some types of intellectual labor I'm imagining here (which may or may not all fit neatly into the "questions" framework).
"Serious" questions could range from "take an afternoon of your time" to "take weeks or months of research", and I'm curious what the actual going rate for those two ends of the spectrum are, for LW readers who are a plausible fit for this type of distributed work.