I would like to see ESRI support cloud based licensing for those that would like it. The main advantage would be that as long as a computer could get to the Internet, it would be able to access a license (much the way ArcGIS Online currently works with a secure login). If it could not access the Internet, then it would give you a specific amount of time for you to run the software without just blocking you out totally. If you were overdrawing on licenses it would keep track of that overdraw and either let the user know and stop the execution, or allow them to continue while sending a note to the account representative noting the overdraw. If you think that this plan is far-fetched, Bentley does this extremely well with Microstation. In Microstation you can overdraw licenses, run while not connected to the Internet, and get a complete report of usage and utilization all from a web interface.
Just think, there is no software to install, update, or manage, it is managed by ESRI so the license numbers are always accurate, you are given generous grace periods, overdraw on you licenses for a brief time (you will be asked to purchase additional license after X number of minutes of overdraw) and you can pull usage statistics from a secure web site (Customer Care portal). Again, cloud based licensing would be available to those that would want that option.