There's a new way to get thousands of local points of interest into your web maps: the CloudMade Data Market Place. There's a fee for using the data, but otherwise it's as easy as the standard CloudMade API (our CloudMade API profile). For a few hundred dollars per year, you can add any restaurant in the U.S., hospitals in the UK to your map, or one of about 80 datasets.
One of the bigger challenges with anything having to do with software-as-a-service (SaaS) applications is how quickly they can sprawl out of control. Before most organizations realize it they wind up with multiple silos of SaaS applications that are even more difficult to integrate than traditional enterprise applications.