Just an update. I didn't exactly solve my problem with sharing my object cross-context. I eventually decided there were too many dependencies to make it worth it to get it working. It was all a lot more complicated than my post showed, since the object I wanted to share was connected to all sorts of other objects.
However, I was able to share a small HelloWorld class that only had one method that I got working, and perhaps it would help you. Each application can *not* have the object in its own classpath.
What I did was take my HelloWorld class and package it into a jar. You must put this jar into tomcat/shared/lib or tomcat/common/lib. After doing that, I put the jar into my lib directory of my applications so that they would compile. When I deployed the applications, I did not include the jar file in the build. This is important, because the classloader will check each individual applications classpath before checking shared or common (tomcat documentation gives the order the paths are checked).
It is necessary to do all this because each application has its own classloader.