Perhaps you'd be better served to find out why your server startup is so slow. Also, you do know that you do not need to stop and restart the server to re-deploy a context? The manager application allows you to stop and start app contexts individually.
Set to true if you want Catalina to monitor classes in /WEB-INF/classes/ and /WEB-INF/lib for changes, and automatically reload the web application if a change is detected. This feature is very useful during application development, but it requires significant runtime overhead and is not recommended for use on deployed production applications. That's why the default setting for this attribute is false. You can use the Manager web application, however, to trigger reloads of deployed applications on demand.