Hi Max,
For what I know Eclipse doesn't support nested dependencies. I've done it with maven support but this simply adds a list of projects / jars into "Deployment Assembly" of the webapp. This way Tomcat adapter restarts when a deep dependency changes, say webapp -> dep1 -> dep2, when something inside dep2 changes the application is restarted. The restart feature can be controlled per application in Server Properties and then Modules tab -> "Auto reload" column. When the restart is disabled then it works just like "Incremental publish" in JBoss exploded application.
The regular expression thing would be what I'm looking for. It would trigger automatic restart on content change. With exploded application content if that is possible.
Thanks for following up,
Konrad