Ask HN: Suggestions for Making Enterprise Java More Enjoyable

I'm currently a university student and do programing work for my University. Since the stuff I work on was also written by student programmers, it has become pretty ugly over the years and my boss wants to do a rewrite over time of the webapps we're in charge of, (email and phone systems).

The situation: Java stack. We have to connect to LDAP, Exchange (we're transitioning from 2007 to 2010), Oracle SQL and a Cisco Phone Call Manager. We've been transitioning to Spring for a while now and away from Tapestry. We also use Hibernate. We have some C# code to interface with Exchange, as well as some SOAP that my coworker manges to communicate with Exchange and the Cisco call manager.

The boss wants to fully transition to Spring. I will work on this for the next three years, so I want it to be as enjoyable as possible. Two questions:

1. If we have to use Spring, what are your recommendations for other enjoyable technology alternatives to do what we are doing?

2. If we could do anything, JVM-wise what would you recommend? Play or something? I don't know. Scala would be pretty cool (or even Clojure) but I think my boss would have trouble finding someone to maintain my code once I leave ...