This month marks the fifteenth year that I have used Quicken to track my personal finances. I previously used a now-defunct program called Dollars and Sense, and before that I just kept a lot of money in my checking account and hoped that I wouldn't bounce any checks.

I recently upgraded to Quicken 2003 For Home and Business, the latest version of Intuit's personal money management software. Crammed with features, Quicken 2003 is designed to woo three groups of customers: Intuit's own, who must be goaded to upgrade from older versions of Quicken; Microsoft's, who must be persuaded to switch from MS Money; and all of those potential customers out there who don't use any personal finance software at all. But to compete for the first two groups, both Quicken and MS Money are getting bigger-and buggier-and are in danger of losing an entire generation of new customers who are finding simpler and more appealing solutions elsewhere.

Intuit and Microsoft are also increasingly offering services once the domain of financial institutions, from bill payment to brokering. But the banks are pushing back, with Web-based software that enables customers to manage their accounts online. After trying all three options-Quicken, Money, and Web-based software-I've concluded that there is no conclusion: each choice benefits different users, and we all benefit from the competition.  I really wish there were a "best of breed," but right now it's just not out there.

The Soft Sell

Overall, my relationship with Quicken has been grudgingly successful. As a freelance writer, I depend on it: practically every dollar that I spend is logged in Quicken's database, with the hope that it somehow will yield another 50-cent tax deduction. To help keep accurate records I charge practically everything on my credit cards, and dutifully download the transactions every few days. What's more, with a wife and three kids, tax laws dictate numerous separate investment accounts for retirement, college savings, and estate planning. My net worth is far less than a million dollars, yet for some reason I have more than 40 different accounts that I track with Quicken-the majority of which are set up for download.

I started with Quicken on DOS, moved my files to the Mac in 1992, and then moved to Windows in 1997. Each of these moves was quite difficult: even though the Mac and Windows version have the same name and similar user interfaces, they have different file formats and entirely different underlying database engines. To move data between the two versions of the program, you must manually export each checking account or credit-card register as a QIF (Quicken Interchange Format) file, and then import each file on the other side. This is an error-prone process that frequently results in both lost transaction detail and duplicated transactions-quite a technical feat, if you think about it.