Now management has spoken and it MUST be this way:
localhost:8080/ (is the home of myapp) aka /webapps/myapp/index.jsp
localhost:8081/ (is the home of yourapp) aka /webapps/yourapp/index.jsp
localhost:8082/ (is the home of everyonesapp) aka /webapps/everyonesapp/index.jsp
all under the same tomcat instance
I tried to just play with the connector such that:
Congratulations, Dilbert! Have they received their "Best Management" trophies from Catbert yet?
There are several ways to handle this. One is to setup port forwarding so that while the external port ID varies, they all get rerouted to port 8080 in the server OS. If they hadn't decreed that the context names must be removed, some OS's could do that using firewall rules, but since you actually need URL rewriting, you'd need a proxy or Apache+mod_rewrite.
The other (and MUCH uglier) way is to setup multiple virtual hosts. You can't just add Connector elements, you actually have to define new Host Elements, and maybe even Engine elements (I'd have to RTFM to remember). And did anyone think to check to see if HTTPS is going to be required? That's another set of ports.
Neither TCP/IP nor J2EE nor Tomcat were intended to be used this way. Otherwise you'd be specifying port numbers in URLs all day long. Yes, you can do it, but it makes life much more complicated for a questionable gain. And it's going to take considerable time and effort (= money) to set up and support.
Customer surveys are for companies who didn't pay proper attention to begin with.