I was preparing to do our taxes last week. Every year in late March or early April I realize that there's an account or two (or three) that I never got around to reconcile or maybe even download activity for, so lots of tedious work ensues.
Vani's been scanning lots and lots of documents into PDF files; I can't recommend getting a scanner enough.
I use QuickBooks for my corporate accounting and like I only sheepishly admit that I really like the new Radiohead album I'm also reluctant to admit that QuickBooks works pretty darn well for me.
Personal finance software though. Geez. Is Moneydance really the leading Quicken alternative? I tried it briefly and it seemed even more painful to use and I use a ~3 year old Mac version of Quicken!
Some of the banks are really awesome with letting you download activity from a long time back and having the statements in easily downloaded PDF files. Bank of America (who I otherwise generally loathe) and American Express are in this category. Chase (Amazon Visa) are notoriously not. Oh man, don't get me started on Chase.