Sorry for the late reply, been busy with the v10.9 release of the Winstep Nexus dock and Winstep Xtreme.
And, people don't pirate $5 software.
Oh yes they do! That's were you are wrong, they will pirate anything that costs money (even only $1) if they can get away with it.
The only way you can stop them is by making the process of finding a pirated copy that actually works more hassle than it is worth it. And the funny thing is that, in their eagerness to get advertising dollars, the pirates are doing exactly that by posting a ton of fake 'get xxx serial, crack, etc...' pages on the web for popular software. Add to that the risk of infecting your system with a virus and/or a Trojan and you have a nice deterrent - but one that isn't strong enough.
On the other hand, if people can find a *working* pirate copy of your software just by typing its name in Google and having it show up on the first page, then have no doubt that sales will suffer. It's a delicate balance.
Stardock is also not pro-piracy like you seem to think. No business is, by definition. It's just that some companies, in their fruitless efforts to put a stop to software piracy, have gotten to the point of seriously inconveniencing the *legit* customer with their limitations, DRM and activation schemes. That's what Stardock (and I) are dead against.
Also, one of the reasons used often to legitimate software piracy, that 'what if I don't like it or it sucks' doesn't fly: plenty of software is trial based these days and it *still* gets heavilly pirated. You sir, may be an occasional pirate, but at least you are an enlightned pirate (or on the way there).
Most people who pirate software are not like that - they simple don't care who they are hurting, in truth, the very thought that they are actually hurting another human being (or a group of them) doesn't even cross their minds. Which is why I advocate that this should be treated as a cultural issue and that our children should be taught in schools and at home that software piracy is evil and hurts people. Go to the root of the problem.