Our system is very similar to that used by Aaron McGinnis.
I’ll add though that I have a Neat mobile scanner that doesn't leave my sight. I keep it in my backpack with my laptop and can scan anything anytime and anywhere I get some free time. This could be in an airplane or while watching TV. The important part is to keep up.
As soon as I get a receipt, I immediately write its purpose on the front. If it involves several categories or classes, I write those too. If you wait a day to do this I promise you won’t remember what it was for. In the case of deductible meals, I’ll note the attendees and business purpose of the expense on the back and anything else that’s relevant.
Everything gets scanned, front and back (if necessary) as a PDF and put into a Dropbox folder. I don’t use the Neat software because its proprietary and I can’t see receipts offline or on my phone. For the same reason, I don’t scan receipts into Quickbooks. Plus, I fear the QB file will become huge (yes?/no?).
Each pdf is labeled with the date of the expense or bill, the name, and the amount. For example:
2013 01 06 Lowes $27.33.pdf
Annotated with the property(ies)
2012 12 25 Verizon wireless $140.57.pdf
2012 08 23 BofA Deposit $4515.98.pdf
This pdf will include a scan of this receipt and previously scanned copies of the associated checks and stubs, plus any correspondence.
Sometimes I’ll add the date it was paid to the end of the name, especially for credit card receipts. This makes it very easy to find on a CC statement:
2013 01 10 La Vecchia $92.81 2013 01 27.pdf
Using year month day format keeps everything chronological.
I’m currently experimenting by adding these file names to the memo field in Quickbooks but it’s not clear that this is necessary (your thoughts?). As long as I have a date, name, or amount, I can easily locate a receipt in no time by doing a file search. Running a QB report of the relevant transactions is all I need to quickly gather receipt images. This also means I don’t need many Dropbox folders.
Then, all paper with anything identifiable on it gets thrown into a “to be destroyed” box and shredded about once a month. If you don’t know someone who uses a shredding service, you can bring a pile of receipts to Office Depot for a few dollars a pound and they’ll do it. I find that most normal home office shredders are just not heavy duty enough long term.
The best part is my desk has never looked cleaner and I can now run reports and find receipts in seconds.
It’s almost life-changing.
Jeff