I’ve worked with some pretty rotten software, but management software is easily the most user unfriendly, so my vote goes to HPSM.
Several decades ago, it must have been as good as other comparable products on Mac OS. And when there‘s no compatibility, the switch isn‘t that easy. You basically have to build your templates from scratch.
That being said, we have decided to switch to MS Office, but my boss will probably use Ragtime until retirement.