Thanks for all the insight, Jim. To answer your questions...

1. Acceptable outcome.

For me, an acceptable outcome would be getting chances to innovate and develop software instead of fighting fires for other people who can't tread water. The way I'm going to pitch it to our department manager is that it's a resource allocation problem. Our team is adequately staffed (well, it's staffed higher than any other team in our department) but the resources are allocated such that the same two people (and I mean two people) handle 80% of the urgent support requests. At the same time, we're given project work (the dregs of the project work) and expected to finish it on time. When that doesn't happen (because we're pulled off saving everyone else's ass) they bring in some of those other people whose asses we were saving to finish up our work. You know what happens when someone finishes your work for you? It ends up being terrible quality.

So I think if I can pitch it that way, it comes off less like I'm feeling slighted (which I am, but that doesn't play well with managers) and more like I'm concerned about deteriorating quality of our software (which is also true.)

2. How to accomplish

I've already had a meeting with my manager where I tried to bring this up, and she very coldly and callously told me "you've been given opportunities." Which is farce. I have numerous examples I can bring up which illustrate the problem, but she refuses to acknowledge it. I have another meeting with her tomorrow, and I'm going to bring up the fact that I'm going to meet with her boss. I'm not sure how much I'll tell her about what my topics will be, because frankly that's between me and him, but I will tell her that it's an effort to discuss issues related to work satisfaction and career goals that she hasn't been able to adequately address with me. I'm hoping that's a good happy medium between telling her too little (and appearing sneaky) and telling her too much (and giving her an opportunity to pile on a bunch of BS to support her position.

3. Willing to risk it all?

Yeah, I'm willing to lose my job if it goes bad. But I can't imagine that happening unless I wanted to leave, or felt too uncomfortable about the situation. The team, including the manager I'm going over the head of, knows how valuable I am. This is also a company that's nearly world famous for being loyal to its employees (we've never had layoffs, ever.) I don't plan on looking like an attitude problem when I do this, I plan on bringing issues up in a professional but direct manner, and finding out what my department manager can do to right the situation. But if, for some reason, this ended up in a situation where I fell out of favor enough that I'd want to leave or be asked to leave, I would be okay with parting ways with my employer. God knows the economy's picking up right now, and I've kept close enough to the job market to know I have a wealth of options available.

So yeah, I am going to meet with her tomorrow and at least inform her that I'm going to talk to him, how she interprets that is up to her. I'll give her a chance to give me straight talk about the issues, but given that I already tried this before, I know what to expect.

Anyway, thanks for your very good advice... Sounds like it's definitely a risky proposition, but with the way my job is now, and the other options that are out there, I feel like I've got nothing to lose.