When using DinkToPdf, had issues where random pictures would not render whether only 1 image or multiple were in the html being converted. The picture could be moved anywhere in the html, above other pictures or below and still would have the same issue.
Issue on github is similar to this - https://github.com/wkhtmltopdf/wkhtmltopdf/issues/3715

My issue was the filename, the filename of the image contained square brackets '[' or ']'. These symbols will be find in the HTML generation but when converted to PDF, the render will fail.
In my case I was uploading files to Amazon S3, the files are then joined into an html file using cshtml; and with DinkToPdf, I generated a PDF from the corresponding cshtml.
I have tested all other symbols, square brackets seem to be the only issue.
Square bracket open:
Square bracket close:
Any other Symbol: