Besides errors in the log, is there a process that can be monitored that will indicate previews in Share have stopped working? I am using Alfresco CE 3.4.d, built from source on Ubuntu 10.04 64-bit with fontbox and pdfbox-1.3.1.jar and under moderate use (10-12 users) we experience frequent loss of preview functionality requiring an administrator to restart tomcat6.
I would expect there to be a clue in the log file.
You may also want to turn on more debug logging.
You may also want to monitor with JMX. While Alfresco JMX is an Enterprise Only feature which is not available in community, tomcat and the JVM will support some JMX monitoring.
Other tools are Jprofiler and the debugger, but try the above two first.