We think this is a great idea and we're discussing internally potentially adding that to the console.
In the meantime, if you'd like to get an assessment, please feel free to open a support ticket (https://tailscale.com/contact/support?type=other&subject=sec...) and we'll happily take a look
May y'all continue to be customer focused.
1. Help them remember why, so that they aren't confused the next time they re-run the checkup. ("Oh yeah, we wanted to do X but we can't until we retire Y because it's not compatible.")
2. If it's clearly labeled as info also shared with Tailscale, product managers could use it to help generate theories about why certain customers don't do X.
For any software or tooling with a complex config, my ideal would be to have a superset of this feature, to provide "intelligent diffs" between full or local configuration states. Whether active or saved. So I could compare not just my current active config and your current recommended config(s), but also between your prior-version recommended config(s) and current recommended config(s). Or between my current config and a prospective new config I'm working up. Or between my last-year active config and current active config.
That's where I'd like to see this sort of checkup. Yell at me please if i just said anyone can ssh as root from any node!