You can map the file directly here without uploading it to Google Drive. If you prefer to map it from Google Drive, you’ll need to use the Google Drive “Download File” module first, then map the file from there.
I’m very new to Make so could be way off base, but my guess is it’s only working once because the filename you’re passing to Wordpress from the HTTP module is the same name every time: file.jpeg. So Wordpress has likely cached an image for that filename the first time you uploaded it, and is just calling the same image again. Or, is not letting you overwrite it, which you wouldn’t want to do anyway because that would break your previous post.
I would try to grab a unique name for the filename, from the URL field in the RSS module. You’ll probably need some regex to parse just the filename out of the whole URL. Or you can create a random filename each time.
In above image you have mapped url from an array. That will always take first url only. You need to use an iterator before http and then map url from iterator.