Maybe it was just my own personal lack of foresight, but I never seemed able to correctly categorize expenses at the time where I entered or reviewed them. Inevitably, I would review everything at tax time and find either deductible items that I had missed, or categories that included a mix of deductible and nondeductible items. If I was going to do that review anyway, it seemed like a waste of time to spend too much effort on the weekly categorizing. I guess it's like the pain of ripping a bandage off quickly, rather than trying to pull it off a bit at a time.
It might seem that it's "safer" to use PC-based software to manage your finances, since your data is not out on the Internet but just kept on your local drive. Well, except for one little detail: Nearly all the information you need is already online. Money and Quicken depend on being able to communicate with your local bank, brokerage accounts, credit card companies, and the like so that they can pull down the data about your accounts. Without that feature, you'd be left to type it all in again.
A few years back, I switched to fully online money management with no PC software other than a browser. There are plenty of options for doing this; many banks, credit cards, and financial institutions offer online bill payment and money management. I like it a lot better. Yes, Quicken or Money have better categorization and integrate all the accounts, but it doesn't seem worth the extra hassles and cost of the software.