"Ideally it would be something where I can move the position/window around, but it would only jump when the playhead hits wherever the min/max of the window happen to be at that moment."
This is what i’d use sah~ for.
I made this thing long ago and the title of your post reminded me of what I was thinking back then(just to clarify, sample-accurate ‘coding’ is actually very easy compared to sample-accurate ‘patching’ which is the real problem here ;D …just saying, you mentioned not knowing low-level DSP, but you may find that coding this sort of thing in C for an msp external is actually easier than whittling it out in patch form(the syntax and techniques for manipulating control data and audio data are much more similar than trying to find parallels by remembering the right max/msp objects)… but of course, you have to learn a bit of C first… but really not that much… i’m rambling…). This patch might be useful for you, but I apologize in advance for the messiness. And you could always replace the windowing method with something else(that’s just the old granular synthesis example hanning window method, i use cycle~ for windowing like that these days…). This patch uses zigzag~ and sah~ to stay within signal domain throughout.
Anyways, didn’t have time to read every post here… sorry if mine is redundant. In hopes that it may help, though… (try the "RandomPreBySegment" or something like that in the menu above the presets, i forgot how much fun this patch was :)