I think it used to comes down to Quicken vs Microsoft Money, but now there are some free options like Mint.com, and probably a few others.
I tried Quicken around 2007/2008 for about a year, and it was really helpful after the year to see where all our money went. However, I would frequently run into issues that seemed like software bugs or things it wouldn't let me do, which kind of turned me off. I had a friend that loved it and I really wanted to love it, but it eventually became too much work and I discontinued using it after the first year.
I've actually been thinking of retrying Quicken again. I'm sure things have improved, so curious to hear other opinons.