I have a friend who runs a pro studio. Once some time ago his iLok went faulty at the same time as the iLok server went down. It took him well over a week to even be able to use his software. He lost clients, reputation and thousands of dollars.
Granted the chances of those two things happening at the same time are small but the fact is, it did happen. Any system that relies on this is madness in my opinion. For every piece software that requires an iLok there is an equivalent thing that does not. I have a beautiful and powerful setup that has no such iLok anywhere in sight so it can be done. Plus it is all off line 99% of the time too which is also a great thing. Any programs that have to be on line to work also represent bad design.
The new cloud iLok system might be the go though. That would be the only thing I would consider. I have also very rarely met anyone who jumps from computer to computer and pulling their iLok key out and inserting them into different machines. That just does not happen much in reality.