Monodraw

>I find it unlikely that such copy protection would actually convert a non-paying user into a customer.

I used to think that but then kept tripping across customers who ran multiple copies of my software after purchasing a single license. I now wish I'd tightened the DRM from the start.

I think you're missing his point. If you tightened DRM, would those customers that ran multiple copies pay for multiple licenses?

Fighting piracy is generally not worth it. Those people would never pay, so you're fighting to stop a pirate from using it, not to get them to pay. There's a big difference.

I have had a handful of people request additional licenses (at a discount) for the purpose of running my software on multiple.

Yeah, it's unclear how many people fall into that bucket. I'm sure it's non-zero but I don't know if it's worth the time.