While there are arguably both advantages and disadvantages with the debian package system (or any linux package system for that matter), it is certainly usefull to be able to “aptitude install whatever” by basically only having to know the name of the program you wish to install.
I don’t think that windows will ever have quite as big library of automatically installed programs, but Ninite certainly does create that feeling, as it is one of most successful and user-friendly attempts to do automatic installing in Windows.
It is an automatic and customizable installer of mostly used programs for windows. After configuration, it will automatically download latest versions of the software such as Skype, Open Office, Mozilla software, other browsers, messengers and such and such, automatically click away all adware/toolbars. It is mostly useful on new installations, but it can also keep your usual software up to date. It is of course completely free, definitely worth a try if you haven’t already!