You gotta hand it to Microsoft. They try. Back in the day I wrote about how impossible it was to figure out where signatures lived in Outlook 2007. There were menus to open and click through to find a major feature buried six levels down.
So in 2010, which I was just upgraded to, I had to find my signature. I was in the main mail window, and started looking. I looked at every bleeding menu. Nowhere to be seen. Finally, I asked a coworker for guidance. He told me to open a new window.
If you open a new window, "signatures" is right out in the open, and easy to see and find. This is an improvement. The issue, however, is that this is counterintuitive in two manners. First, it is accessed from a completely different place as in 2007 and before. How hard would it to have a link to signatures out of the main window without opening a new message? So, you know, we can find it. Second, when I start with a new program, I want to set up my signature before I send my first message, not after. Now, I have to open a message, set up my signature, and is it in the message? No. I have to close the message and open another.
So with thousands of hours and lines of code, they have gone from having something completely buried but accessed from the main window, to something not buried at all, but accessed unintuitively from the new message window.
Progress. Maybe by 2020 they'll have signatures readily available in the main window of the program.
Or maybe we'll all be on Gmail.