Cleaning Windows

To start off, things not to mess with:

Component cleanup

Component cleanup using Dism.exe
Get current component store size:

Dism.exe /Online /Cleanup-Image /AnalyzeComponentStore

Clean the component store (can make a lot of room):
/ResetBase removes previously installed packages/updates for a deeper clean, but prevents uninstall/rollback

Dism.exe /Online /Cleanup-Image /StartComponentCleanup /ResetBase

Useful things to check at your own discretion

cleanmgr.exe
%SystemDrive%\$Recycle.Bin
%LocalAppData%\Temp
Downloaded files
Log files
Old chkdsk files

Notes for OS older than W8/2012R2

if dism breaks, good luck :)
you may need to install KB2852386 to clean up some Windows Update stuff via cleanmgr.exe