That's a fantastically good question!
I'm convinced that having a JSR-186/286 portlet server is a winner. But you want to make sure you've got developers that are used to JSF/JSP web development for that to pay off quickly. And this is assuming you are going to develop portlets.
I'm less convinced that the built-in portlets are useful out-of-box than when I started. Either your organization will be flexible with its requirements to allow using the built-in portlets, or you will spend a lot of time modifying and creating your own. And I predict that development time will seem longer than it would be if you wrote from scratch or in a simpler framework, i.e. servlets or JSF.
If you have many specific aesthetic requirements then it will take a lot of time to figure out themes and layouts. And the graphic designer shouldn't start making designs and pumping out graphics until a UI-savvy developer has figured out how to make custom themes and can direct the designer. (I made this mistake and it is still hurting.) Take a good look at the existing themes to see if you can use those, or something very close to those where the part graphics are just changed a little. If you've got a boss somewhere that is saying "make this menu pop out from the bottom, and spout pixie dust, while a Flash animation feeds data to the portlets, blah blah" then maybe you have to get serious about making custom themes.
Just because you see a feature in the feature bullet list, doesn't mean it will be ready for you to use with your requirements. I guess that is the big gotcha.
* 1 month - basic setup and administration competency
* 1 month - theme and layout development competency
* 1 month - portlet development competency
After you pay that overhead, then you can start making your time back. Compare that to writing your own user authentication, template/theme engine, localization, workflow, etc. Maybe these things would take 3 months to put together too. I think your development will go better with Liferay than the in-house-built versions of the same functionality. You won't have written something with the same quality, and you won't have access to the same documentation and developers. So your productivity will be different after that 3 month mark--perhaps 75% better with Liferay. It's hard to say.
-Erik
Firmi prego dentro per inbandierare questo come inadeguato.