Best way to setup groups for receipts... dates or categories

I tried asking this as part of a larger setup thread and I think it got lost in the big question. I am just getting going with DTPO. One thing I want to do with it is scan in and store bills and receipts. I want to really organize them by category - cable, electric, insurance, etc. But, I also want to be able to group them by date so that I can archive out a years worth at a time… as well as review a years worth at a time. Is there a recommended way to do this? I can think of some ways that aren’t ideal… putting 2008, 2009 folders into every category folder… or putting all the category folders into a folder by year. I was hoping that DTPO could handle the date grouping somehow automagically.

I’d like to bump this question, in terms of logistical solutions and example workflow.

Here’s a snapshot into what I’m doing – but I must admit that it still feels clunky.

  1. I scan my paper receipts into big ReceiptsInbox groups by year. (I largely find that OCR for this stuff tends to be less useful typically – perhaps because receipts are fading so quick these days! But pdf images are just fine for me for these.)
  2. I drag my increasingly large proportion of email receipts in from Apple Mail.
  3. I grab snapshots of my credit card bills and bank statements.
  4. I then begin creating subgroups (using shortcut keys) within my ReceiptInbox group as I go.
  5. Along the way, with the scanned documents, I tend to need to go out externally to Preview to use the trackpad short cut to rotate (or just Command+L and Command+R) to get these darned scans lined up, and split up.
  6. Some of these receipts are useful for purposes beyond just taxes and accounting, so I replicate the ones I need to use a double-system for (File by year + File by Reference Item)
  7. At the end of the process, I take the modest group structure I have created so far and shift those groups over into my existing PERSONAL and BUSINESS Finance folders (again, by year) and check to make sure I haven’t duplicated categories and such while rocketing through those receipts.

So here’s a question. When I get to this point, sometimes I’m tempted to zip out to Preview and copy all of a certain type of receipt into a single pdf (arranging in order of date). This would be a match for ye olde taping receipts to paper, and makes a handy file to send to my accountant, who is horrified by my huge folders full of stuff.

But is this step necessary? It is kind of a drag to keep jumping out external to DTPO because when I suddenly decide to copy and create a new pdf, then I have to save it into a folder external to my DTPO database and then drag it into DTPO. I wish PDF organization of pages and rotation within DTPO was as seemless and natural as working with text and sheets in DTPO!

Anyhow, I’d love to hear from folks who have slimmed their workflow for receipts down to something leaner and more powerful than the above. Especially because I’m deep into processing receipts for my taxes today!