Last things first: I'm not prepared to answer as one of "us folks." I'm only speaking for myself here.

I think those are great questions, and any quick, easy and obvious answer to any of them probably isn't going to help much. When I've found myself stuck, what I've usually wished is that someone would tell me where to look for the answer. More often than not, what I've been offered instead has been someone else's answers: that here's what's wrong with me; that the trouble with me is that I'm too much [the way I am] and not enough [the way someone else wants me to be]; that I do too much of [what I do] and not enough of [what I'm obviously supposed to be doing].
It's hard to fault someone for doing or saying the "proper" thing. Personally, I find I react to the "proper" thing or to the not-so-"proper" thing however I react. If I'm ever disinclined to go along with someone's suggestions, one of the first things I check for is whether they could just be doing the "proper thing" as a routine to cover up that they don't really understand or aren't really interested.

I think there are many kinds of "honesty" -- or, more accurately, many different contexts for honesty. If I can't stand someone, I could argue to myself that I have a choice between doing the "proper" thing (e.g., saying nothing) and doing the "honest" thing (e.g., telling them I think they're a jerk). Probably neither would be very helpful to them -- unless, of course, they noticed me tying myself up in knots over what to say to them and successfully inferred what it might be that I wasn't saying.

The kind of "honesty" I just mentioned is probably better, but not much better, than deliberate deception. If you and I are in competition, I could tell you you're a jerk, whether I think your are or not, in hopes of throwing you off your stride; or I could tell you you're a jerk because I honestly think you are and it would do you good to realize it. In the latter case, I could even pat myself on the back for being "honest". Either choice would actually reveal more about me than about you, if you were open to noticing it. Neither would be at all supportive except to the extent that you chose to draw support from it by discovering that you could shrug off my non-support.

As I see it, empathy, too, depends a lot on context. If at some point you were to say you were stuck, there'd be different ways I could empathize with you (or not). I could picture myself feeling (my idea of) stuck and focus on how I hate feeling that way (and how you must, too). In the process, I might end up communicating that, just as I don't know how to get myself unstuck, you must not know how to get yourself unstuck either, so too bad. Or I could focus on how, when I feel stuck, I often discover an unexpected way out (so maybe you will, too). It probably wouldn't do much good to tell you, "Just look for the unexpected way out!" because most likely, that would only convince you that (1.) I didn't understand your situation and/or (2.) you must be doing something wrong.

I'm afraid the best I have to offer isn't much more than a platitude: When supporting someone, come from your own experience and be prepared to learn a lot that you don't already know (or at least, don't think you know).