>When I was young I did all of my programming on a TI calculator (BASIC, and z80 assembly with an on-calc assembler).
Those existed?! I remember reading articles on Z80 assembly language at ticalc.org as a teenager and desperately wishing I had some kind of calculator-native text editor and assembler that I could use to program in math class -- at least, that's how I would phrase it now. I assumed that none existed, and setting up a cross-assembler was beyond either my capabilities or comprehension at the time (not to mention, at the time programming was most fun in school when I was supposed to be working, not at home on a PC with a million other distractions). I didn't get that assembly language programming experience until years later. Instead, in between games of GALAXIAN and FALLDOWN, I messed around with horribly slow, illegible TI-BASIC, a language so crude that even Pong is an exercise in futility to write in it.
I just searched the ticalc.org archives, and yep, here's at least one such assembler, loaded up with the familiar MirageOS:
http://www.ticalc.org/archives/files/fileinfo/403/40304.html
I'm not going to lie, I'm kinda sad right now, wondering what might have been, if only I had known the correct keywords to search for at the time...
Anyway, I totally agree with the premise of your post. There's almost always too much to configure for novices to get a handle on, and novices don't know what the hell they're supposed to be looking for in the first place. If setup involves one step too many, or the novice is expected to figure too much out on their own before they can start, they think "I'm stupid, why can't I do anything" or "these programs are stupid, I wanted to implement that thing I read about but I wasted X hours setting up this completely unrelated thing and copying magic commands," and you'll likely lose them for good.
Which is, incidentally, why I think anyone that prefaces their programming tutorials with "you should learn to use a real text editor like vim or emacs" deserves a swift kick in the ass.