Where did you get pairs from? If the Pikachus reproduced by binary fission (splitting in half and then growing a new half, like cells do), or had 18 genders, they would still evolve. They only have to make copies. Doesn't matter how.

> No, they're all created by the mad scientist but can think, reason, communicate, teach, interact, invent

If they can't reproduce (and/or aren't made of stuff that can reproduce), I would say complexity of behavior is irrelevant.

For example, the identical iPads coming off the factory line are still technology, whether they are loaded with simple software or complex software. The complexity could go all the way up to AI, but they would still be technology.

Note that we are used to "intelligent" meaning "alive", because the only intelligent thing we know of at this point in history (us) is alive. But I think it is perfectly valid to suppose that non-living things could be intelligent or even conscious.

> So if an iPad [...] created a new, slightly different iPad, would they be considered alive?

Yes, under those conditions they would certainly start evolving, and I think that's a perfectly reasonable line to draw between technology and life. In this new example, the "phenotype" of the iPads would change in a self-sustaining way, emergently, independent of any design or intent.