The fact that Raymond Chen is debugging these kind of issues, tells me Microsoft is short on staff that has his particular set of skills, handing him the hairiest issues from the annals of Windows. The new hires are probably all about .NET and JavaScript and what have you -- whatever Microsoft is about these days. I doubt it's C/C++. Chen is probably on standby and is paid handsomely as a de-facto VIP consultant. He is a legend, but he's becoming somewhat of a vintage developer.
Managed dump analysis in windbg was a thing. It’s been many years since I’ve needed it, though. Service telemetry improved quickly thereafter.
I do wonder how Microsoft will manage the transition of the NT generation. Raymond Chen has been doing this kind of work for thirty years. He probably has, what, another ten years, max? Who are the next generation of Windows gurus that will take up the mantle?
Hanselman is good on the blog part, but not in Chen's class re Windows domain expertise. And Windows is not, despite all that is said, going away anytime soon. I think this could be a real problem.
Hopefully there is a set of 25 year old developers in the Windows team who have deep and growing skills in Winternals, and Microsoft have the good sense to encourage them in their career.