OP here, thanks for the thoughts everybody.
@miles running - I am intrigued, but not familiar with the distinction between flexibility and mobility. Sometimes I will run at 6:00 pace, early into an easy run, while focusing on my form. I feel like it loosens me up, but it's not always enough to prevent IT pain from creeping in later on.
I've been going to a chiropractor every 8 weeks, he says he targets mostly my Piriformis, and psoas to a lesser extent. I used to do just one stretch per group, but I've found that several stretches, and more dynamic ones, really help a lot.
My dream is to one day have IT bands that feel loose as damp string, where I forget they are there. I hate having to even think about them, they've ruined so many runs.
@Jed - Stretching muscles cold could be part of my problem, I usually find the best time is before bed for me. Partner stretching kinda sounds romantic, I'm going to ask my wife if she would consider it!
I'll check out Mobility WOD, it sounds like a good resource. Now that Ryan Hall is a cross fitter I'm going to have to eat paleo and join a box. I sincerely hope Ryan is trolling, the alternative is too hard to consider and I would have to join him (cognitive dissonance).
I'll look into Tim Anderson.
I'm also thinking about standing more at work, the desk thing seems dumb.