Modulars aren't really intimidating at all, if you ignore the way they look. Certain things can be (the 200e has a pretty steep learning curve, especially if you haven't worked with modulars before). For the most part, unless you have absolutely no understanding of synth architecture, you'll be able to pick up the basics of using modular gear pretty quickly. It's all really straight forward, unless you get into really complex digital logic modules and other crazy shit, but I can't see anyone getting stuff like that for their first setup.
DIY stuff is easier than you'd think. There are plenty of resources out there that could guide even the most retarded of human beings (e.g. tiesto and armin fans) through a basic project.
I've never looked at it as a progression, though. Just different tools for different purposes. I'd never turn to one of my modulars if I wanted polyphonic pads, for example (unless I wanted to sample them for that purpose). That's what my microwave xt, andromeda, prophet vs, etc... are for. I'd also never turn to my Metasonix PT-1 if I wanted something to play in key (or stay within 2 octaves or so of "in tune").
Max/MSP never intimidated me much, but that's probably because I've been coding most of my life, and it just kind of made sense and forced my computer nerd and synth nerd sides to mesh and become one. I think the max for live idea was idiotic, though. There are going to be a lot of Ableton users scratching their heads after buying it, thinking it's just another instant gratification plugin.
Kyma is a great system. It would be a waste for most people, though. Lucky for the rest of us, those people usually end up selling their systems off cheap.