I should also mention that it isn't in-house IT, but a separate company, and the whole thing was set up in a rushed effort late on a Friday afternoon the week before the whole working from home business would start (our management slept on it until the last minute), with a lot of other companies requesting the same support from the IT company at the same time.
Not that it completely excuses everything, and as you can tell from the Windows 7 PCs it was never the most secure setup, but simply to explain some of the reasons behind the mess.