For me it's usually about availability. If someone suggests I try out a cool game that came out in the 80s, there's a pretty good chance piracy is the only way to play it. Sure, you can pay way too much on Ebay to get a physical copy, and I have a fair collection of retro games, but it's not like the money from Ebay sales go back to the original creators.

Same with movies. The version of Star Wars I grew up with, the one without all the digitally added stuff since the late 90s, isn't on Disney+. If Disney announced a nice blu-ray Star Wars collection that featured the copies without Jedi Rocks and the extra aliens in the cantina and whatever, I'd go out and get it. But they haven't, so I stick to the fan-made 'despecialized editions'.

I don't pirate from the little guy. I buy albums on Bandcamp and indie games on Steam all the time. I want the small creators to be able to eat. But I'm also fortunate enough to have a little disposable income. I know some people pirate as much as they can, and while I don't entirely agree with it, I don't know their financial situation (or the availability of these things in their country), so it's not really my place to judge them.