In the Tavern (where the mSO folks sit all day and watch this site with eagle eyes), at least one person expressed concern at this recent question - App to alert me of firmware updates on a rooted Android phone.
What's our policy on such questions?
I believe that we should treat these questions just like we would any others. They aren't really special, and jailbreaking/rooting is not illegal (at least in the US). I don't see a need to make a special case for these.
We aren't really in a position to judge the legality of a motive. That's the job of posters, not us.
I noticed a distinction worth pointing out in your original question. There are two areas here and I would treat them differently:
Questions on how to jailbreak/root (techniques, usage, links to software that will perform jailbreaking/rooting, etc)
Questions on software that does other things on a device that has previously been jailbroken/rooted
Questions of the first category, I would consider to be more of a gray area. SE's canonical treatment of these gray areas is to just allow them, to avoid the chilling effect of trying to censor things that might be illegal in some places. But I would still be more cautious with this first type of question.
Questions of the second category, in my mind, are completely acceptable, as they deal with doing stuff with your device after you've successfully rooted it yourself. The topic of the question is not "help me root" or "give me software to obtain root"; it's "help me do this neat thing with my rooted device". I don't think these even fall into a gray area at all; they're just flat-out acceptable (unless they have other quality problems with them or are off-topic).