> 0. Forget about tracking things down to the dollar, or even the tens of dollars. That level of precision is unnecessary. If a coffee here or there is going to break your budget, it's already broken and you need to go in to panic mode.
I use Homebank[1] which has pretty useful auto-assignment rules. I then have vague categories - think groceries, lunch & dining (e.g. buying lunch is more luxurious than buying lunch and dining is even more extravagant)
Every couple of weeks I import my statements and have a quick look at anything that wasn't auto-assigned - there's usually a couple of things and I add these, based on the merchant name or description, never to worry about again.
I figure this gives me the best of both worlds.
The only reason this small amount of work works for me is that I don't have to pay cash for much. When I do, it's unique enough I remember and categorise it, no biggy. I understand this wouldn't work for most though.
I wouldn't want to lose track of the small things, as they do add up! Keeping the categories loose (and not caring about the difference between coffee and a sandwich) makes it work.
"Look after the pennies and the pounds will look after themselves." as my grandma always says.
[1] http://homebank.free.fr/en/