Tomcat can "not start" in a number of different ways. It can literally not start (launch the Tomcat application), in which case you should see an error message on the Tomcat start command line.
It can also "not start" in that the Tomcat application launches, but fails to continue. You may see a command-line error message, but you should also check the TOMCAT_HOME/logs/catalina.out and localhost log files for error messages.
It can "not start" in that the Tomcat application comes up and runs, but web clients cannot communicate with it. You should see an error message in the catalina.out log file saying that one or more ports were in used by some other program.
It can "not start" in that the Tomcat server starts up OK, but the web application doesn't come up. URLs sent to it return a "404 Not Found" page. The catalina.out log has a progress report on the deployment and will have one or more error messages indicating what defect exists in the webapp deployment descriptor or WAR kept the web application from starting.
OR, everything might have started OK, but you're expecting the debugger to say something. When you do external debugging with the no-wait option (suspend=n), then Tomcat would start up, but you would have to manually log your debugger into Tomcat via port 8000. That would connect, but not do anything. You'd then set breakpoints or whatever to catch code executing and do the normal debugging stuff.
Sometimes the only way things ever got fixed is because people became uncomfortable.