Oracle Portal woes
It can be challenging to work with any big software vendor, but Oracle in particular does not seem to be making portal projects easy for its faithful customers. I've previously pointed out the new emphasis on Oracle WebCenter Suite in lieu of Oracle Portal, which will have a significant impact on the large existing customer base.
Recent commentaries from the blogosphere also support our findings in the Enterprise Portals Report about complicated appserver upgrades and spotty documentation.
In my many interviews with Oracle Portal customers, a repeating theme is the difficulty in finding knowledgeable portal resources, even inside Oracle. The lack of dedicated portal coverage among Oracle's many technical blogs would seem to confirm this.
Common risk factors apply to all portal projects, but at the moment Oracle seems to be making things are bit more complicated.