I definitely think web2py is much more productive than that stack. However, 
it's worth considering if the migration is worth it. In my company we still 
support one app that has a backend like that, I always wanted to migrate it 
because it's the only thing still using Java. Frankly, even though it 
annoys me that I have to keep running tomcat on my server and some Java 
knowledge in my head, I could never justify it because the changes to the 
backend are so rare.  
  
So, really, the first caveat, is it worth it? Are you going to make a lot 
of changes to the backend?  
  
Then, if you'll be migrating one endpoint at a time you will also have to 
deal with routing the requests. You can avoid it completely by running the 
web2py and java versions completely side by side, in different URLs, and as 
the web2py version gains more functionality you can update the mobile app 
to use the web2py version. In a bunch of iterations you would have 
everything converted and you would always be able to downgrade the users to 
the previous version of the app if something went wrong. Of course the 
better option, if you have people experienced configuring the webserver or 
you're willing to learn, is changing the webserver config so that the new 
requests for a given endpoint go to web2py without any changes to the 
mobile app, which is preferable as it's much faster to switch back if 
something goes wrong.   
  
Another thing to watch for are table migrations, make sure to have them 
disabled as you probably don't want web2py changing the tables for the 
application during this transition phase.

Good luck!

-- 
Resources:
- http://web2py.com
- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
- https://code.google.com/p/web2py/issues/list (Report Issues)
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