Applications made by smaller companies are not impossible to break. They're just smaller targets that are generally not worth the effort.

Windows doesn't make most of their money off regular folks installing Windows. They make their money from businesses buying licenses for all their staff and from computer makers buying licensees to preinstall windows on your HP laptop. They want normal people to just use Windows by default so they don't care if the guy that built his custom gaming rig doesn't pay for Windows.

It is twofold

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Part of it is that EVERYONE wants Windows. So obviously piracy groups are going to crack it

Whereas comparatively few people want a specific CAD tool. So piracy groups aren't incentivized to crack it.

Because if you actually read a .nfo file (that you obviously found in church on a sunday while minding your own business), most warez groups are obnoxious little shits who only care about the clout.

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The other aspect is that, for stuff like Windows, Microsoft doesn't actually care about piracy. They basically throw licenses at consumers for free (hell, I am still cycling through like four different keys I got during college). Because there is so little profit in what OS Grandma buys that it doesn't matter.

Instead, they profit off keys sold to the people who sell pre-built computers (so laptops and prebuilt desktops) who just treat that as an operating cost. And, more importantly, they sell bulk licenses to actual companies. And THAT is a lot of money

And you know what encourages Reynholm Industries to buy hundreds of Windows and Office and so forth licenses? The fact that their employees are comfortable with that OS and ecosystem... possibly because they grew up with an unactivated bootleg copy.

There's not much of a point in overly restricting the windows OS.

End users who don't want to pay for it anyone are just going to find a workaround.

It's the OEMs and corporate users where Microsoft makes their money, and who also lucrative targets for legal action if they are using it unlicensed

It's a similar strategy to how Adobe has protected their creative suite products: they rather have college students and personal enthusiasts familiar with that particular software than fight tooth and nail enforcing licensing on the average person.

The more things the software tries to do the more potential gaps appear in the system for it to be cracked and the larger the data pool the more people who are trying to crack into it.

Probably part of it is that the small company can make it have onerous security that is harder to hack. For windows to have onerous security will mean lots of computer downtime as people try to figure it out. That is more costly for Microsoft than the lost revenue of a few hacked systems. They are more interested in ensuring corporate clients are paying for windows.

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Well you also have 'cracked versions' of these apps! For instance, in Android you can download an APK file, the equivalent of Windows EXE and install the app's full version. If this is an app which doesn't require subscription etc, you are all good to go!

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That's because the biggest tech companies have the resources to invest heavily in security and they are constantly updating their products to make them harder to crack. Smaller companies don't have the same resources, so their products are more vulnerable to being cracked and used for free.

That's because it's much easier for hackers to break into large companies with more resources. Smaller companies don't have the same resources to protect their products so they rely on paywalls to make money.