The question is what do you want attach to README. I think, the most popular cases are screenshot images, a logo file, etc. In this case I think the repository is a rational place. But if you want to store many images, for example, for the documentation needs or .psd files ;) I think you need to put your files outside the repo.
I look at that problem like a the ratio of the work cost to impact to the future. If I knew that my files are not often changed, then I would put them to the repository. In the opposite situation (bad long term impact) I would put them outside.
Of course in this strategy the key is the good sense. And this you can only gain by a bigger experience.
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The question is what do you want attach to README. I think, the most popular cases are screenshot images, a logo file, etc. In this case I think the repository is a rational place. But if you want to store many images, for example, for the documentation needs or .psd files ;) I think you need to put your files outside the repo.
I look at that problem like a the ratio of the work cost to impact to the future. If I knew that my files are not often changed, then I would put them to the repository. In the opposite situation (bad long term impact) I would put them outside.
Of course in this strategy the key is the good sense. And this you can only gain by a bigger experience.