I feel comfortable saying I could learn, but if the job expects me to come in with a working knowledge of Adobe Acrobat, I will feel like an idiot and not apply.

Okay, so, I see Tiny Wittgenstein there. And even if I'm wrong about that, I'm not wrong about the fact that every job in the tech sector asks for more skills than they really expect to get. I have never in my entire career met all the requirements in a job posting that I've applied to, including the job I hold now. Tech companies reward arrogance confidence.

I feel very badly as though everything I know is out of date. It may or may not be true, but it's demoralizing.

*hugs* I don't know that I have anything useful to say to that. My problems/brainweasels around job hunting are somewhat different.

I don't assume I can't. I used to learn human languages at above-average speed. I don't know if that would correlate to computers.

I know one person who had a good experience with http://startupinstitute.com/, and several people who have hired Startup Institute graduates. The local Python users' group also does occasionally crash courses specifically for women who are learning computing for the first time. Would you like me to forward you information the next time they host one?