BTW, if the answer to "does this make you uncomfortable" (or a variant on that theme) isn't clear, treat it as if the answer was "yes".

I think that's a very good rule. In general people don't have nearly as much of a problem expressing that everything is all fine and good than they do expressing that there is a problem. If they're not comfortable saying that they're comfortable, well then chances are they're not comfortable. Sounds much more obvious when I put it that way, doesn't it? :)