Quicken 2004 is up to its old bugs again -- auto classifying every transaction incorrectly, creating myriads of nonsensical transaction splits. I clean it up and then it does it again. It also threw a memory exception; I had to 'copy' (rebuild) the database again.
I really only use Quicken now to download my credit card transactions and check transactions. I've gone back to spreadsheets for overall finance work and tax reporting, and given up on balancing the checkbook.
I've used Quicken since DOS version 2. It was a great piece of software then, though some DOS versions had nasty database corruption bugs. After about DOS version 4 it started downhill, and it's been sleazing about for years. One day I'll abandon it completely.
Progress in software is not guaranteed. The personal web building toolkits have never returned, that market is gone (iWeb doesn't qualify). Finance software is pretty meager on the PC, and non-existent on the Mac. Word processors aren't as good as they were 10 years ago. Photo management software is, of course, far better. Overall though, it's a mixed picture.