Is convincing employers to transition technology stacks really something that is generally considered easy (or even doable)? I'm stuck maintaining 'enterprise' software running on VB6 and ColdFusion 9 and the idea of getting my employers to sanction a migration to something newer is laughable.
Not necessarily, but convincing your boss to be mindful of your medium-term career goals definitely is and at largish companies there should be opportunities for you to spend time working on something else. Career-wise, I'd be more concerned about working for someone that wants you to stagnate than about the specific software you're maintaining. (Not saying that that's necessarily the case, BTW.)
It's a thing. I don't know about convincing employers, but employers do it. I've participated in such projects. hell, I know people who have done such things in government and military contracting contexts. It does happen
so yeah, it happens. Legacy systems are re-written. convincing your employer? yeah, I've never seen that part happen, so I can't say anything, but I certainly have seen the aftermath.