The licensing process for the ArcGIS server is way too complicated. Every time my license expires, which I don't event know happens unil I look in my logs, it takes me multiple phone calls and over an hour to upgrade my server with a license key.
1. Send automated messages every so often until the server license has been renewed or cancelled
2. Provide a very simple process to renew a license on my server. Ideally it should just go out and check when it's expiring to see if the license has been renewed, or just send me the key I need in an email. I shouldn't have to spend an ungodly amount of time trying to figure out how to do this!