I don't believe so. I know you can create a deeplink to a specific request offering. I also know that you can make an attachment mandatory...but I know of no way to have a file already attached pragmatically.
If one of my users asked me this question I would ask in return: what the reasoning is for having the PDF attachment required on the offering when it might be easier to have whatever the PDF contains, as fields on the offering itself?
That's what I figured.
To your question, in several cases I was able to reproduce the form within the offering, but we have some cases where that isn't possible (yet). We have some that are long and complicated, and the current request form designer just isn't advanced enough. It is certainly possible that it is I who isn't advanced enough... ;-)
If you'd like (and it's not confidential), feel free to email me a PDF you're having difficulty with, I might be able to suggest a form design to overcome your issue.
I appreciate that Ashton.
We have two complex, multi-page PDF forms for requesting access to custom applications that list over 100 access roles, with two options for each role (add, remove). In addition, each of those roles are owned by one of maybe 15-20 people who must approve new access. Building all the logic and workflow to handle that would be a huge task, and the HEAT form would be overly long, so that's why I was hoping for an command to 'create a request and attach this file to it'. Maybe this will be possible in the future... ;-)