This is one of the more frustrating things about buying legitimate software; having to deal with annoying DRM schemes.
It's especially frustrating to think that after paying hundreds of dollars for a piece of software, someone who downloaded it for free is not only saving that money, but potentially enjoying a superior experience by not having to deal with the DRM.
This can be countered through value-add propositions where the delivery and/or continued support of the software can offer a compelling trade-off versus downloading a free version. I look at Valve's Steam store as being a primary example of that.
I agree with your first point about the CP being the single most dystopic aspect of what is otherwise a miraculous, marvelous technological capability.
I don't share your second frustration. I pay for what I use, look for sales, it costs what it costs, and it's irrelevant to me whether someone else got it for a better price or for free. Whether someone downloaded the software illegally or whether someone got a comp because they did a review or whatever, what's it to me?
I'm neither a developer nor a capitalist, but I do not understand why for-profit companies wouldn't be better off thinking of revenue as revenue, and focus exclusively on the people who buy their products rather than worry about the people who don't.
For example, I have never had nor will I ever create an iLok account. Since I don't use pirated software, this means I don't have any of the products that require it, which in turn means that those companies get zero dollars from me. If I were a pirate and downloaded DRM-free versions of their iLok infested software, they would STILL get zero dollars from me. Since 0 = 0, how does whether or not I am a pirate make any material difference to their revenue stream from their point of view?
If, on the other hand, they dropped all of the CP nonsense and embraced the Free Software idea (free as in freedom to use, not as in free of charge) it would open up a whole new market (however large or small) of people like me who would now potentially buy their software. Those who want to pirate would obviously still do that, but this is already happening now anyway, so it's difficult for me to see the downside of giving up "protection" that fails to protect.
Thankfully, there are still many developers who do offer righteous ease-of-use, local license numbers or key files that give us the freedom to use the software independently from remote servers, offline, making it exponentially more reliable and stable, and making it easy to transfer content to a new computer or whatever: Cockos/Reaper, Valhalla DSP, Klanghelm, AudioThing, uHe, ToneBoosters, Garritan, Melda Production, Fabfilter and Hornet are just a few that immediately come to mind. These companies have somehow managed to stay in business without harassing their customers...
...So I have to believe it would be possible for the others to do this as well. But they would perhaps have to give up a capitalist control freak mentality or something. I'm confident that the biggest barrier to righteous software commerce is psychosocial, not economic.
For people who freak-out over the idea that someone else got a better deal than they did, or a deal that you don't think they deserve, I would suggest reading the
Parable of the Vineyard Workers in the biblical New Testament. The story is about people who have exactly that problem.