I can attest that when I was living on a few hundred dollars a month as a CS student, I pirated a very early version of the IntelliJ IDE. I don't feel bad about this, especially as I've been responsible for tens of thousands dollars worth of license sales for the same product over the years - if only a full-price version of IntelliJ was available, I'd have stuck with Netbeans/ Eclipse instead.
I question this, purely because the "Open Letter to Hobbyists" shows Microsoft as pretty hostile basically immediately.
I would bet good money the same applies to graphics people and Photoshop.
There were certainly better ways to do DRM at the time (even now) that Adobe was well within their monetary limits and interests pursuing. But of course, it was still cracked.
Also, for a hundred buck fee and some TPB/Demonoid credit, it's almost always worth it to a cracker to go after a flagship product.
There's also the running theory that Adobe was the one to release some of the cracks, namely because new releases of the Creative Suite back when it was new would be cracked nearly "instantly".
It's speculation, but the above theory would make a lot of sense - and, in my opinion, that's exactly what ended up happening, and what made Photoshop the industry leader over a pretty decent selection of alternatives at the time (though admittedly PS had already mostly established itself at the time anyway, but it could have probably been swayed).
I know some of those old friends stuck to Adobe while others looked for open source/free alternatives depending on budget/revenue. I think one even works at/with Adobe these days after trying to hack on more features more than 10 years ago. But it's the same reason Apple/Google want kids using their devices in schools. Train the next gen to want your product and let the marketing flow.