After I graduated, I worked on a hotel site for a certain large three letter US news company. Now, back in those days, a website was just seen as an extension to brochure advertising. And for the majority, nothing has really changed in the intervening decade.

One of the first things I've noticed is that when working for a Blue Chip, there is a very strong disincentive against doing things the Right Way. This is because the clients will ask for what they think they want. This is usually not what they really want, and is pretty much always miles away from what they need.

Should a login system be case insensitive?

Short answer: Yes. But numbers/symbols should be required.

Long answer: One of the most common mistakes made when logging in is to have the caps lock key pressed. In studies, significant proportions of support calls are simple case-sensitivity issues with usernames or passwords.

Some login systems address this issue by detecting when the username and password are all uppercase, and displaying a message "you entered your username and password in all capitals."