Of course, that has nothing to do with whether or not piracy is right.
Stealing an operating system and digital audio workstation—which can both retail from anywhere between 100 and several hundred dollars—is a moral failing. It’s wrong to do that, no matter what sort of income you have, and how many other people do it. In fact, the more thieves there are, the more a company like Image-Line is losing on their software. It’s never right to take another person’s property without their (real or implied) knowledge and permission.
Now, I’m not going to say that someone like this is an awful person, because I don’t know them. But they’re giving themselves permission to do something wrong based entirely on selfish reasons. That at the very least should raise concerns about whether or not your moral world-view matches his. The fact that you don’t know each other in real life adds at least 82,982 other red flags, quite frankly. You can’t properly discern these things behind a computer screen.
Confronting him about this is probably only useful if you genuinely think he would actually listen to you. For some reason, you know his rationale for stealing—he’s poor—and so I suspect this has already come up in some capacity.
Turning him in, well, I have no idea what would happen to him. Honestly, I don’t know what to do about that. You’re not Catholic, but if I were you, I would go to a trusted Priest for council. This is moral minutia that I’m not educated enough to analyze on my own.
But there’s also the option of simply cutting the friendship short, on the grounds that you and he have moral world-views which are at odds. Obviously, we have sinners in our lives, and we ARE sinners. But if you feel romance flames coming up, I would encourage you to think long and hard about the notion of being comfortable stealing when a person thinks they’re safe to do so. That doesn’t strike me as being remotely Christian, and I think people who follow Jesus should try to build their future families with those who do the same.