Powershell + ChocolateyGet (+ DSC if you want) does a pretty good job already. Apart from specialized software it's been years I had to install via tedious hunt

Powershell + ChocolateyGet (+ DSC if you want) does a pretty good job already. Apart from specialized software it's been years I had to install via tedious hunt for link + download + execute + go through wizards or similar. That being said, the meat of it is 3rd party so not having package management builtin is a valid complaint. Then again, if you think about what that would take: non-trivial.