With W2008 and newer, there are zero activation cracks that don't get patched, so people who pirate are pretty much stuck with W2003 if they want security updates.
Not sure about 2008, but 2008 R2 can be rearmed indefinitely. Not quite as good as an activation crack since it requires rebooting to safe mode to run a script to reset the rearm count every couple months, but that's no big deal if someone really wants to avoid paying for something.
And as stated before, ads are not the only thing that can cause a message to be deemed a commercial electronic message, so it's not as simple as "do we have ads? no? then it must be ok to send".
If it's easier for you to blame Microsoft than to realize this legislation is a real problem for many organizations, then that's cool, you're entitled to your opinion and I'll stop trying to change it.
(I just posted relevant quotes in a message above this one if someone wants quick reference for the two definitions).
For the purposes of this Act, a commercial electronic message is an electronic message that, having regard to the content of the message, the hyperlinks in the message to content on a website or other database, or the contact information contained in the message, it would be reasonable to conclude has as its purpose, or one of its purposes, to encourage participation in a commercial activity.
Then "commercial activity" is defined as:
"commercial activity" means any particular transaction, act or conduct or any regular course of conduct that is of a commercial character, whether or not the person who carries it out does so in the expectation of profit, other than any transaction, act or conduct that is carried out for the purposes of law enforcement, public safety, the protection of Canada, the conduct of international affairs or the defence of Canada.
Then there is no definition of "commercial character" so you're at a dead end. If you call in and ask, they say they have no clue, it'll be up to the courts to sort it out if/when lawsuits are filed.
But, no, you're not going to be sent to prison for years over a $49 theft.
Tell that to Issac Ramirez. Sure, it was a $199 VCR and not a $49 whatever, but yes with some of those crazy three strikes laws you may find yourself in prison for some pretty stupid reasons. http://en.wikipedia.org/wiki/Three-strikes_law#Cases