I guess for me, the path I'd eventually like to take is an either/or thing. A TT job would be great, but an R&D think-tanky job would also be great. I don't know if others think of their "what ifs," like "what if I had decided to do this at the normal age?" but all you have to do is look at CVs of people the same age as you who are in TT positions, then compare your CV to theirs. Yes, sure pursuing a PhD would have resulted in more papers published, conferences, classes taught, etc., but in my case it also would have resulted in much less real-world industry experience. When I looked at CVs of professors my age, I realized that they had little-to-no industry experience, and I wouldn't want to be in that situation either.
Which gets us almost back to the original subject of LORs/CVs for us older people. When I was re-writing my long-form CV (as opposed to my short-form resume,) I was stumped as to what to put in the papers published, conferences, classes taught, exhibitions, etc. I mean, I had nothing to put in that section, even after completing my master's. So then I looked at all the high-profile industry projects I had worked on since the early 90s, and reformatted those in CV format and listed them instead.
Not sure how impressive that was to adcomms, but I thought it looked pretty good.