I would like to see Liferay's out of the box experience improved by taking steps forward in areas where there are known solutions.
For instance, in the Windows environment, a Liferay download bundled with the required JDK dependencies. Remove these unnecessary steps between the user and the product, even if it's only for Windows users at first, because it's a step in the right direction.
For another instance, when running Liferay for the first time, instead of showing us our site, make a special, easily accessible tutorial driven site that navigates people through basic Liferay tasks like signing in, adding applications, configuring a page, and then also links them to our tutorials, videos, wikis, etc. Throwing our entire site into their hands is probably a little overwhelming.