Chocolatey is a package manager for windows.  This is something that I think all windows users should consider getting.  Even if you don’t use the command line there is a GUI to interact with it https://chocolatey.org/packages/ChocolateyGUI.  You can add new packages to chocolatey.org and take advantage of their automatic packages to make it so if you update the package the users that have it installed will automatically be updated.  Awesome.  So, if I ever have to manage a bunch of computers I think this is the first thing I’ll install on all the windows machines.

Would be nice to have program that would connect to all of the chocolatey computers and ask them for the packages that chocolatey is managing and also request that particular packages be installed on those machines.  This would make chocolatey perfect.

https://puppetlabs.com/ does that!  And its open source http://puppetlabs.com/puppet/puppet-open-source (at least for the non-enterprise version).  However, there are a bunch of alternatives http://alternativeto.net/software/puppet/.  Which is cool.  Might be a better/easier/free alternative.