Those R4 carts were all over the place. I was living in Japan at the time and everyone and their mother had one. There is no doubt it cost them a lot of money.
I bought the device primarily so that I would have full access to my complete library without having to tote around physical security tokens everywhere.
And that is the same reason I have hard drives and alternative loaders for my PS2 and Wii. I can play any game that I buy without getting off the couch to switch discs. And with the Wii, there is the added benefit that I probably won't have to open it up and replace the optical disc drive for a third time. This has the unfortunate (for them) side effect that it is dead simple for me to pirate games on those platforms if I had the inclination.
So in my particular case, it would seem that the most effective anti-piracy measure would be to remove the requirement that paying customers have to continually juggle physical tokens to enjoy the content that they paid for.
If I have to break the security features in order to add the convenience features that I want most, the psychological barrier for piracy is lowered. If everything that I want is already on this side of the fence, I am far less inclined to jump over it.
It just so happens that Steam provides the feature I like, which is easy access to a whole library. As a result, I have on a few occasions preferred to re-license a game I already own on disc through Steam, just so I won't have to dig up the physical disc, configure a DOSBox or WinXP VM, install drivers, make tweaks, download the official and unofficial patches, and such.
I already have more games than I have time to play games. If I go to pirate something, it won't be because I don't want to pay, but because I don't want to be hassled every time I want to play.
So the number one anti-piracy measure from my perspective is DON'T WASTE YOUR PAYING CUSTOMERS' TIME. That applies equally to unskippable DVD scenes, physical disc checks, and connection-always-required schemes. Don't waste my time, and I won't go looking for ways to stop you from wasting my time. It is impossible for you to irritate me into giving you more of my money.