I experimented with this as well, but since I was keeping full copies of the discs on my hard drives anyway, it was unnecessary in my case. I still have most of these disc images; now on my NAS.

I think the first time I tried N64 emulation must have been in late 2002. There were indeed still games released for this system at the time, although not many. Tony Hawk’s Pro Skater 3 (ported to the console in 2002) was one of the last big games for it. Fun fact: The PC version at lowest settings looks almost identical to the N64 port.

Early N64 emulation was spotty, but the fact that it worked at all absolutely blew my mind, especially since I was just in the process of switching from N64 to PC as my main gaming platform. Super Mario 64 was one of the first titles to be properly playable with next to no issues, but outside of that game, it was a bit of a gamble and remained so for years. Performance could vary wildly, glitches were very common (some titles remained unplayable until surprisingly recently, like the excellent voxel-based Command and Conquer port for the system) and the plugin system proved to be a nightmare, as it fractured development resources.

GameCopyWorld is still around today and still being updated. Looks the same as it did decades ago.

My go-to method was to create a disc image of games from the local library and then use either DaemonTools’ copy protection emulation feature or a crack from that site. They had and still have a really good selection of the latest titles (nothing 18+ though, the equivalent of the American M-rating), although it’s almost entirely console games now due to mandatory online activation with most PC games.

There was also software (probably still is) that records the state of your computer before using a program. Then you’d run the program and it recorded any changes (with filters, of course), which you were able to undo with a simple button press. At the time, it was usually a change to some registry entry. This was another method I used to reset timers and usage limits of software like the one you mentioned. As before, I tracked down registry changes by hand until I discovered a more convenient option. This was necessary, because many programs with usage limits left information behind when uninstalled so that you couldn’t just do what you did.

I could swear I did something like this (although obviously not at a kernel level) decades ago with trial versions of software that would only work for 30 days or similar. At first, I did this by hand for the entire system, but I’m pretty sure I had a program for Windows 9x that could independently set time and day for any given application, without affecting the rest of the system.