Someone would just NOP out the check and publish a cracked version on the internet, so everyone who can't crack it will be able to download the cracked version.
Maybe for a regular single user who probably wouldn't of bought the product, but in an enterprise company it's a whole other story.
I myself pay for software I know I could of looked up a crack for, but being a developer I know how much effort software development takes I opt to either find an open source alternative or buy the product if reasonably priced. If I can't find a decent alternative and the price is poor, I probably wont use it, whatever it is.
I think the point is that the only way to make your software genuinely resistant to cracking is an onerous DRM scheme like you see with games or obscure engineering software. Stuff that takes a lot of work to implement (or $$ to license) and more importantly actively annoys legitimate users.
Anything short of that is probably going to be cracked for software that is even modestly popular. I think setting the bar just high enough to keep grandma from breaking it is pretty much just as good as something more sophisticated.
The psychology of it is, you can't stop nefarious users ultimately. But you need something that at least makes honest users take some extra action specifically to crack your software. Making them feel like they are pirating something will stop most honest users.
I think it comes down to what is easier, faster and most convenient to do -- download a cracked copy from a bittorrent site or jump through the hurdles of ordering a legitimate copy.
There have been many companies/independent developers who have used the "warez scene" to intentionally "leak" and distribute their software. As the software gains traction they make it easy for the user to buy a license so they can update the software from within the software. Otherwise the user has to wait until a new cracked copy gets released.
You'll never ever stop anyone from cracking your software but convenience does come at a price.
Except the legitimate distribution channel doesn't have to be easier than the illegitimate one, it just has to be easy enough. There are plenty of incentives to use the legitimate channel, all you have to do is not make it too annoying.
I never knew anybody who wasn't able to get around licensing AND downloaded cracks. Cracks are (were? is that still a thing?) just time savers. If you can follow some tutorials on replacing a binary with an edited one, you are brave enough to learn how to edit it yourself.
Also, that user is running some random binary from the internet just not to pay. Without that crack, you would never have had that user.
It depends on who the customers are. We have license checks at my company, and they would be rather trivial to circumvent. But they are there to keep the honest people honest, not to stop a determined adversary.
Just because it is there doesn't mean people will use it, especially when you are creating B2B software. If a company was found using cracked software that would cause big problems for them. It is cheaper for them to just pay for the software.
I myself pay for software I know I could of looked up a crack for, but being a developer I know how much effort software development takes I opt to either find an open source alternative or buy the product if reasonably priced. If I can't find a decent alternative and the price is poor, I probably wont use it, whatever it is.