Normally, you can drag an image file from e.g. Windows Explorer and drop it directly into the Comment editor. The image will automatically be inserted in the comment. Sometimes this doesn't work for the following reasons:
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You have Windows Vista or later (e.g. Win 7 and 8) and you run Visual Studio as administrator. This is a known issue.
On Windows Vista and newer Windows Explorer runs with medium integrity level. If you run Visual Studio as administrator (high integrity level) then for security reasons OS will disable drag and drop from Explorer to Visual Studio.
You can either run Visual Studio as normal user or use an alternate file manager that can be executed as administrator. For other possible solutions see http://stackoverflow.com/questions/15226600/visual-studio-does-not-let-me-drag-drop-items-into-it. - You have Windows Vista or later (e.g. Win 7 and 8) and you open the comment editor as a modal dialog. Visual Studio doesn't allow drag&drop in modal dialogs in Vista and newer. You need to set the comment editor as modeless window in VSdocman options.
If none of the above solutions is suitable for you, there's one general workaround. Use copy&paste instead of drag&drop. Select the desired image file in Windows Explorer and copy it by pressing CTRL+C. Go to the comment editor and paste it by pressing CTRL+V.