I started a project called Issue-Bidder (https://issue-bidder.com/) with the same concept before I even knew that bountysource (and meanwhile also tip4commit) existed.
I do not collect any repositories from Github but rather let the users manually submit a repo to Issue-Bidder.
And at this point I think there is only one reason why bountysource does the opposite: For marketing reason – or better let's say this straight-out: the intention to make money. Guess what, the opensource community (speaking as a set of all specific communities) is a high potential and open market. Everybody is able to move mountains if you're ruthless enough. Let's just take this post on reddit as an example: http://www.reddit.com/r/gamedev/comments/2dsvme/someone_stol... and I'm sure tons of other example cases exist out there.
In my opinion we can compare bountysource and all the other vultures out there with the financial brokers back in the 90' (why did I even set a filter to the 90' anyways?).
Should we now all hate them? Or are we now just hating around because we are naive and didn't restrict all our repos and do believe in the positive aspects of this high potential market called opensource?
I questioned this myself as well and came up with the answer: I simply can not.
The point is that the more complex an issue is, the more requirements wont be defined anymore or things just get forgotten to require. In this situations people will/have to interact with each other. Based on this maybe even a sub-issue needs to be created for a specific requirement. If you work on a platform like odesk or so you will act the same way and contact the freelancer by Skype.
This is one of the main reasons why the issue-manager on IssueBidder always has the control to cancel or finish the ongoing issue. I also struggle around with the idea to include the GitHub comments on on IssueBidder as well - not that it's needed but to make things more clear from the beginning.
Not sure if I hit your question exactly. If not precise it more please.
You hit it I think, but the bigger issue (heh) remains: you're basically creating a contract which is not all that different from a tiny freelancing gig, but you've a more distant relation between the parties, so it may be harder to build trust.
Does your system involve an escrow concept? Something like, the money is wired by a third party (you) as soon as the commit is merged into a certain branch, or something.
I more than welcome you (and any other) to suggest any ideas of building trust.
The concept is as follows so far: The full amount of what people want to spend goes to a third party (me). Then the money is wired to the developer or back to the "bidder" depending if the issue-manager accepts or cancels the progress. I hope i made this clear on the pricing page: https://issue-bidder.com/pricing
thanks for the compliment!
i hope people will see the chance to get things solved with this. personally i came up with the idea cause of things like neglected docs.