I started by upgrading GnuCash to the latest version. GnuCash is an open source personal finance program that I like a lot. I never used Quicken, but I had used to use an early version of Microsoft Money (circa 1995), and I like this a lot better. It's available for multiple platforms, has great tutorials, and is free. When I started using it, the Windows version was still in beta, but I never had any problems. The Windows version came out of beta about the time I started slacking off. GnuCash can import Quicken, Money, and csv files, and when I was originally setting up my accounts, I just downloaded the information from my online accounts and imported it. I suppose I could've updated everything by doing that, but I also remember that I still had to spend a lot of time manually going through the transactions to categorize them, along with translating the bank speak in the descriptions into something I could recognize (i.e., replace incomprehensible abbreviations with actual words). I figured as long as I'd have to manipulate them anyway, I might as well enter them by hand.
Saturday I rummaged around for the receipts, then sorted them all into little piles by month. Yesterday I managed to get the last six months of 2007 entered and reconciled. Tonight I started in on 2008, and got January and February into the system. So far, there's only been one charge for which I couldn't find a receipt, and I remembered buying the dinner in question. More problematic are assorted eBay and Amazon transactions, most of which have to be tracked down by rooting about in the depths of my email program, but although it takes time, I've been able to find them all. With a little luck, I should be up to date by the weekend.