You're kidding about VBScript, right? Short of abusing Scripting.Dictionary in some rather awful ways you can't even define data structures in it, and writing code that spans more than one module involves the use of some obtuse XML crap (.scs files) which most people don't even know about. VBScript has its place but using it for anything other substantially more complex than short straight-line automation scripts is lunacy.
No, if a kid with an internet connection wants to start programming stuff then in some senses the ground has never been more fertile. Even if you're not willing to leave Win32 you can quickly and easily download IDLE or a win32 build of Ruby, and the latter has plenty of really gentle tutorials to ease a novice into the world of programming, to the point where the interested reader could probably stumble oneward from there through Wikipedia well enough for most of the intermediate concepts to stick. The sort of things you can easily accomplish with MinGW and a bit of Googling today would have absolutely blown my ten year old mind back when anything above the level of BASIC was a forbidden art unheard of outside of obscure BBSes (which show up on your parents' phone bill) or a university library.
On the other hand, a modern PC environment is a frightfully complicated beast compared to an Amiga or a Spectrum. That I think is far more of a problem than the availability of simple tools and documentation these days... that and a more comfortable consumption-oriented environment on a modern desktop that doesn't force you to make your own fun.