I'm not gonna sharpie 250' of cable. I'm sure my customers would rather have a pristine cable than one with my crappy sharpie work all over it. 
As for the connectors, finding them isn't the problem, it's finding them cheap. Mouser's got some from FCI on there. It's $88 for 200. I'd rather pay more like half that. My budget is running kinda thin here, and I'm sure there's some surplus somewhere I could buy or a supplier in China I can order from.
As for the shrouded headers, those are for my customers so the won't plug stuff in the wrong way. But if permanently attach the ribbon cable with the right connector then I don't really need to worry about that.