[cunninghamd]

Couldn't you just wire up a graphics library in Python, and give him a Sublime Text editor configured so that CTRL+B runs his python script? I'm not sure reinventing the wheel on this one makes sense, considering the power and simplicity of some of the environments out there, PLUS, python would provide him with real-world skills.

[sdegutis]

I want to give him the most frictionless experience getting started. And Python has plenty of dark corners that he might run into pretty quickly. Plus I want to spare him from significant whitespace for a while (but significant newlines are fine). That's why I was envisioning something like Ruby but a little simpler.

[vram22]

(Note: I use Python a lot, so sort of biased, maybe ...)

>I want to spare him from significant whitespace for a while

Reasonably smart kids can understand a lot of things if one takes the time to explain it to them a bit, along with the reasons why a particular thing is the way it is.

I'd suggest you try to avoid dumbing things down too much, just because he's a kid. You might be surprised.

Logo (language) could be another option, and is pretty cool for kids (of all ages :) There are free versions available, just google for them or see the Wikipedia page for Logo.

[sdegutis]

It's not about understanding. I'm sure he can understand it just fine. But he's also learning how to use an editor. Throwing in significant whitespace is just going to add frustration.

[vram22]

IMO, that's not such a big deal - understanding what significant whitespace is, if you're prepared to have him deal with significant newlines, as you said. But it's your choice, of course ...