Do not overthink it. Set up paperless, create a watched folder. Paperless does the OCR for you. Scan your stuff and check if it was scanned as you want it to be. If yes, drop it in the folder. Tag as you go, paperless will learn and tags will get more accurate. If something reaches a level where you can trust paperless to always tag it correctly, let it tag that type of thing completely automated.

And file away your scanned papers separately, because scanning old things takes a lot of time and will most likely not be done in a day or two. Even with a scanner which can pull through stacks of pages, you still have to check if every page really was scanned (scanners can pull in two pages at the same time, only one page will be scanned then) and you have to merge multi-page docs (or scan them that way immediately).

I’m not sure exactly what you are looking for but here is my workflow:

1. Laptop - This is where I do most of the uploading to paperless. When I get an important document over email, buy something online that’s expensive enough for me to want to save the receipt, or buy something that comes with a digital manual, I download the PDF and upload the document to paperless in the browser.

2. Phone - I have an iPhone and use Swift Paperless to upload physical mail, physical receipts, or physical manuals I can’t find online.

I know I can set up Paperless to pull documents from my email automatically but it’s not very good at guessing the tags and correspondents in my experience, and because it’s not good at guessing the correspondents and tags, I have to manually edit the documents anyway so I might as well upload them myself. I’ve just got into the habit of getting a document, knowing I might want to view it later, and upload it right then or later that day. The built in OCR works great.

Edit: Oh, my behavior has changed a little because of paperless too. I now ask everyone for a receipt, email confirmations when talking with customer service, or if I’m dealing with a business that only hands me paper documents, I ask them to email them to me too. I’m pretty annoying about it. Basically, if the transaction is important enough to me, it doesn’t end until I get proof that I can upload to paperless.

I organized paperless in the beginning but not so much anymore.

I have given it access to my email inbox and to add attachments automatically. I can then search for receipts and more without having done the work to import it manually

it works relatively well. for sites and services that actually include pdf receipts