The application of updates required manually updating databases. There was an easy-to-use installation procedure but the upgrade process was both not automated

The application of updates required manually updating databases. There was an easy-to-use installation procedure but the upgrade process was both not automated and very easy to break. The developers (at least at the time) were more interested in making repeated breaking changes than they were in investing the effort to allow earlier adopters a reliable upgrade process. My irritation was that this was the metaphorical equivalent of a business offering a fantastic deal to new customers but treating existing customers with palpable disdain.