> I frankly don’t care about being on top of tech any more but I’m keen to use my years of experience being productive.

Preach it, brother! :-D

> In this situation would you do it?

FWIW, if it would keep me productive and keep a roof over my head, i'd not at all be averse to working on VMS or a similarly obscure system, provided they didn't require me to know anything about it going in (which would rule me out).

At some point in our lives we have to accept practicality over bling. Let the young'uns fight out the LLM Wars, then walk in (if necessary) once that dust has settled.

The nice thing about the DEC VAX/VMS system is that there is good help online, and enough good documentation to fill a library.

I run an 11/780 emulated system on my phone on days I feel nostalgic.

I am doing it. Not VMS, but a different niche legacy platform. The jobs are few and far between, but so are the people who can do them. In particular, people who can work on both legacy platforms and the modern stacks are quite rare, and AI's presence means there aren't any more of us showing up in the world.

This is exactly the kind of work where decades of experience still matters.Modern stacks reward speed,but legacy systems reward judgment and cautions.Not exciting but often valueable.