please read here:
you can setup an image upload page, then you could use the Embed Youtube Plugin to parse image URLs to embedded images (sets the <img> tag).
-> I guess the best way is to write your own plugin for that and release it here :)
Today I find a way how to easily implement image upload service together with Markdown editor. The solution is universal and can be used with any text editor.
Here is a link to short tutorial I made about how to implement file uploading. (File uploading is made by using external service)
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