Is it possible for two applications to share the same context root is they're in separate managed servers/cluster?
What if they're in the same managed server/cluster, can you have something like one application use /path1 and another one use /path1/path2
You can technically deploy the same app twice with different context roots, but beware of issues like duplicated datasources (which will cause you problems in Weblogic):
How can I install one Web Application in two context roots in Weblogic 10g?
How to deploy the same web application twice on WebLogic 11g?
However, I believe you can NOT re-use the same context root in one container (in your case one managed server), as this is in violation of the J2EE spec. So the answer to your second question is no. You can see more here about using the same beginning context root value
Here is another decent break down of context root usage from Oracle.
