The ancient software also wasn't bad. After a few months learning the hotkeys and menu structure, the speed with which you can enter and process data was absolutely incredible. It had problems, but usually minor and patched in a reasonable time for corporate IT.
The real problem was their database management. I don't have any information, so I'm assuming here, but my impression is that they're using some positively ancient database software. Doing a backup of the local cache took multiple days, though it didn't lock the DB. Requests to HQ were incredibly slow, about 30 seconds to pull an account record. Larger queries like neighboring store inventory took a minute or two. Running a report on local inventory would regularly take tens of minutes, and it only had to read the local cache.
The database was a few tens of GB on disk. Granted, I don't know much about databases, but if running something like "SELECT * FROM inventory WHERE sales < 100 ORDER BY lastSaleDate" on a 30gb database takes 15 minutes, something is wrong.
There were a lot of problems we ran into on a daily basis, and almost all of them related to database functions. Particularly when a record failed to unlock, sometimes we'd have to reboot the local server, which caused all terminals in the store to reboot. That usually took a good 15 minutes.
Personally, I rather enjoyed not having Windows at work. For the most part, everything Just Works, and given the hardware, it ran ten times faster than windows would have.
My current job is a Windows development shop, and I don't have enough curses to describe the pure rage I feel every time windows does something stupid (which is approximately every three hours).
