I’m not jumping on the elementary OS pricing pile-on, because making money in open source can be complicated. I will say that for a distro looking to make money, the absolute worst time to hit people up is right before they download. Lots of people distro-hop just to try something out with absolutely no intention of using it. It’s like taking a car for a test drive—who would pay for that?. Instead, I’d focus on users six months after they download a distro. Email them. Ask them if they’re still using it. Ask them why they’re not. And then offer them the chance to support the project. Those are the users who’ll pay for the product—because if they’re still using it six months later, they know it has value.