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I am considering to sponsor a development of some particular features in some Open Source tools. I would like the results of the work to be available publicly, and if possible, to be included in the main product line. The features are usually something which is of general use, but not very critical, and no one has currently a plan to develop it. For illustration, imagine I would like to use MinGW for Win32 development, but I miss a post mortem debugging option, I would like this feature to be implemented and I am willing to pay $1000 for it.

Is there some common way how to proceed, or is this wildly per-project dependent? Are there some general guidelines how to contact the product developers, or are there some common meeting places where smart open source people who might interested to participate in such sponsored development meet, which I should visit to advertise the sponsoring option?

Are there some specific ways how to talk about the job to be more attractive to people participating in open source (e.g. it might be more interesting for them to participate in a contest than just to take a payed job, which might have a bit of mundane feel)?

Or perhaps is this something which you think has little chance to succeed, because perhaps money has very little value for open source developers?

Any tips and experiences from someone who has some experience of open source sponsorhip from any side (sponsor or the developer) are welcome.

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For any particular feature you want added, go ask the developer/maintainer what they're up for. Most of them have forums, request pages, or an email link somewhere. Sometimes all that is needed is a request. If it's a good idea, they'll implement it. If it's not that important to them, or they're not up for it, you can also ask any other programmer and see if they'd be willing to dive into the open source project and add your feature. Paying them is a pretty good incentive. There are sites for piecemeal work with bounties like this.

From there, you could theoretically submit the patch to the open source project and see if they want to include it. Or if they still don't want it for whatever reason, you could fork the project. Or just hang onto it yourself and feel special as the one guy with the awesome version.

(Also, have you tried DrMingw, a JIT debugger)

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"There are sites for piecemeal work with bounties like this." Could you provide some links, please? –  Suma Apr 11 '12 at 14:06
    
Sorry, I was in the market years ago, saw the competition was way more hungrier than I, and never really went back. You'll have to search on your own. –  Philip Apr 11 '12 at 14:13
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is this wildly per-project dependent?

Yes, it is. You will need to contact the project maintainers about his and see how they would like you to go about things.

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