Settings provide setting changes and for most users this will not be used very often. This is probably why WordPress has put it in the bottom of the menu. This may include settings specific to a plugin that may or may not be included in the individual plugin menu item.
Tools allow specific tasks to be performed like import and export the content to other blogging systems. The Tools menu has other tools that are self explanatory. I have not used Press This or the Categories and Tags converter to give a fair review.
Global settings and configuration are found in the System menu. Each plugin, component, module also has its own settings. I have had more exposure to settings in Joomla due to system changes that I had to do.
No winner here. But Joomla’s settings do seem much more easier to manage.