>> "How far will he get?"
He'll be able to activate on the first machine. TurboActivate is smart enough to block all the clones (because of our properitary fingerprinting algorithm). We talk about this extensively here: http://wyday.com/limelm/features/why/#competition
>> "How does Turbo Activate behave when this happens?"
It will say the cloned computers are not activated and give the customer a chance to buy more copies of your software.
>> "Is there a way around this without using TurboFloat?"
Yes. TurboActivate by default blocks this kind of behavior.
If instead of "hard drive cloning" (which I presume this question is talking about) you're talking about VM cloning, then the way to stop this behavior is to use TurboFloat. See: http://wyday.com/limelm/help/vm-hypervisor-licensing/