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If you take this route, take the opportunity to write down any customizations, and figure out a way to script them using PowerShell. For the applications you like to install, check out Chocolatey, electric, Ninite, PortableApps, and/or the new official Windows package manager (though this may be just Store apps, I've not used it). Maybe script the app installs so you can script the customizations for your apps, too.
If you take this route, take the opportunity to write down any customizations, and figure out a way to script them using PowerShell. For the applications you like to install, check out Chocolatey, electric, Ninite, PortableApps, and/or the new official Windows package manager (though this may be just Store apps, I've not used it). Maybe script the app installs so you can script the customizations for your apps, too.
No love for scoop? Definitely second your take on regular Windows refreshes. Love Ansible for managing the parts that are scriptable, though DSC has come a long way too.
For non Mac users, Zeal ( https://zealdocs.org/) is a Dash clone that can use the same docsets. Works on Windows and Linux.
Kinda late, but if you're thinking of switching to VSCode, I'd like to suggest using VSCodium instead. It is an open source build of vscode, and doesn't have any microsoft branding/telemetry/tracking. Exactly the same as VSCode in every other way.