I come from the low budget world where sometimes there is ONLY a wide, so it's been difficult for me to let some of those low n' wide shots go without wiring everybody so you hear 'em all the way through the scene. I don't always let 'em go, but depending upon how wide and what I know of the coverage, I begin to relax into the idea that I can do this sometimes without fear.
When it's really, really wide...
When wiring everyone would be a drain on the schedule and suck anyway, so...not wishing to tempt the post production sound gods...
When I know for a fact that the director won't stay in the wide for more than a moment (because I ask)...
When else?
-- Jan