Well aside from the time it totally bricked my system, it pretty good.

I had a number of occasions where Windows on my work PC f-ed up. None of the times, the windows "troubleshooting" wizard was anything but a waste of time before calling IT or digging into the problem myself.

If the problem can be solved by a restart of that thing's service (audio, network, etc.) then it has fixed things for me in the past.

Pretty much no other solution (especially the running old games one) has ever worked in the troubleshooter without me having to tinker with it further.

Even once? Yeah, just that once though. It was on like a dell latitude from 2010 and it wasn't a permanent solution either

The search service on my computer crashes from time to time and the troubleshooter gets it working again without having to reboot (I hate rebooting).

Troubleshooting has never been useful, and I think that was new-ish in XP. Startup repair (and chkdsk) have genuinely been useful.

had a couple of windows 2000 pro and server recovery saves. haven't thought about it since. hrmmm

Not once as far as the Troubleshooting Wizards go.

I think it fixed my MBR once during Win7 days.