This week's book giveaway is in the OCAJP 8 forum. We're giving away four copies of OCA Java SE 8 Programmer I Study Guide and have Edward Finegan & Robert Liguori on-line! See this thread for details.
Please don't repeat your posts. It won't get answers any faster and it pollutes the forum.
There is no such file as "System.out", System.out is one of 2 output iostreams that Java supports for compatability with Unix-like OS's. The other one is System.err. For most purposes, Windows is "Unix-like" enough when it comes to the System iostreams that it doesn't matter.
The console is System.out and System.err, unless redirection is applied. However, the System.out stream for Tomcat is normally redirected by the Tomcat.bat/tomcat.sh scripts to go to a file named logs/catalina.out.
On Unix (Linux) systems, I normally use a command named "tail" to track output written to catalina.out on the console if I want to watch things as they happen. Windows doesn't come with this command, so the process requires you to develop a solution of your own.
An IDE is no substitute for an Intelligent Developer.