Your reader is right, Quicken 2.0 or so for Windows was terrific. Fast, portable (it would run off a floppy, IIRC), foolproof, crash resistant. I was so sold on Quicken + Checkfree, that it took a considerable amount of temptation from my own bank, USAA,  to finally ditch the combination.

I loved it. For years later, I stopped upgrading, and have only in the last 10 years, upgraded a few times, when my current bank (no longer USAA) claims "we don't support Quicken 2004, you need to upgrade to 2005" or some such. What's up with that? Clearly, it's more appealing to Intuit to incorporate bank profiles in recent versions, then providing backwards compatibility for long-time customers.