My (not so large) app can be redeployed on JBoss 4.0.5 exactly two times before the deployment is failing.
I know that the issue of OOME in PermGenSpace has been discussed before and the default answers were either "Sun JVM bug", "use jrockit" (which only increases the available redeploys a little without really solving the problem) or "increase perm space" (dito, I manage up to four redeploys).
I don't really buy any of thse answers because other apps do not have such severe problems.
Here's a nice summary:
Using Yourkit I tried to investigate the problem:
I've added this to the 'For gavin to review thread'