Hmm, thanks for the advice everyone. I didn't see Baileyworks' website until after I posted. And I'm from NH so that just might make me a little biased...
Spent today out on a job site soaked to the skin which reminded me why I started looking at expensive messenger bags in the first place. Crumpler bags seem nice but aren't waterproof so I think they're out.
Feel like I could go for a Baileyworks Superpro L or XL, or a Chrome Ivan or Sultan. But if I'm going to buy either one of these I think I'm gonna have to pound 4 or 5 beers before I get the courage to pull out the credit card...