Upload/Import transactions with attatchments (PDFs)

Issue:

I use Comdata CC for fuel and odds and ends, 100+ purchases a month. I am not a Comdata client, which means I cannot set up Q-S (Quicken-Simplifi) to automatically sync like a bank. I can get my statement and convert it to CSV to upload. However, I am having issues with that being assigned to projects and categories, an issue for another post. Because this is business, I need my receipts, and I regularly scan them into a PDF.
The image shows a portion of my receipts for one or two units (loads) and how I store them with a txt file as a template. This way I don't need to open a reciept to see what it was for, I label it as I scan each one at the end of the day or days.
last four of the CC# - Location meaning name of business - Date - Amount - Catagory - Unit#(s)

Is there a way to attach each PDF to an email and send it to Q-S, or even upload it from a laptop to Q-S online (an idea from using QBO)?
Before you suggest using the mobile and doing it at the time of getting the receipt, my issue becomes that some of these receipts are long and vital info is at the top and bottom, which means wide-angle and pray. The other issue is that the image of my old, shaky hands is often illegible.