I was setting up a network for a family friend's business last night, and stumbled across some of the worst Windows software I've seen in some time. The software has been around since the DOS days, and about two or three years ago, it was completely rewritten for Windows, but some of the DOS-isms remained. Mostly, it had to do with printing.
I didn't immediately notice this at first, but every printer that works with the software has to have a local printer port assigned to it (LPT1, LPT2, etc.) and be referenced by such within the software. It's.... archaic, but workable. My friend has two offices, and they wanted to remotely connect from one office to the other, access the other office's records, and print them locally. Remote Desktop will pass your printers through to the remote host, offering them up as local printers. It even assigns port numbers to them, beginning with TS. Problem is that the stupid ass software ONLY prints to printers who's port number begins with LPT.
Stupid stupid stupid. I want to slap those developers.