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.
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.
let's not only creators get paid for work but great way to revive old abandoned ones.