Is the sys admin job market really that bad?

I'm not arguing with you. I agree with you. In fact I'm getting whiplash from the whole you-need-to-specialize/Know All The Things market schizophrenia. What I'm saying is that you're applying logic to a scenario that often doesn't bother with logic. When I started out doing tech support in the mid '00s everyone higher than L1/deskside was already a specialist because there weren't nearly as many things to specialize in and certs weren't quite the scam they later became, and end-users weren't expected to do anything outside the application they were paid to use. Then a few years later the non-title "IT Generalist" came about, likely invented by an HR drone embittered by their failure in marketing and sold to a C-suite comedian who thought "Why hire 3 when we can hire 1" couldn't possibly have a downside. Then came the DevOps and security and database companies expanding into their own applications realm and the goddamn cloud and everyone wanted specialists again. There are entire companies that do nothing but sell specialized software for *another company's* specialized platform/solution. That's where we've gotten with specialization. I've been fortunate, all things considered, in being trained for a specific sysadmin role in my current position, but no business stays with a solution forever and that makes specialization a game of roulette. If I had nothing else to put on a résumé between my current responsibilities and L1, I would be walking a tightrope and working without a net to say the least. Specializing per se is not "bad", but you'd better have more than one thing to specialize in or you're going to end up at square-one every 3-5 years. You need to have time to learn each one of those things in-depth to the point you can anticipate an interviewer's questions before they ask them. So the question then becomes, how many things can you specialize in before you become a do-it-all generalist anyway?