I don't know about TomEE, but the Eclipse WTP plugin commits atrocities on the server configuration for plain
Tomcat. Then it lets them go stale when you want to update them. I've always preferred the sysdeo/mongrel plugin to run Tomcat. You have to manually create a Context definition for each webapp in the
test, but at least you know exactly what you're getting. Note that newer Eclipse versions don't support sysdeo or mongrel. See recent postings in the Tomcat forum on where to get an equivalent plugin.
The secret of how to be miserable is to constantly expect things are going to happen the way that they are "supposed" to happen.
You can have faith, which carries the understanding that you may be disappointed. Then there's being a willfully-blind idiot, which virtually guarantees it.