An interesting article came across my radar today. It was Satya Komatineni's blog entry on CVSNT, Eclipse, and some lessons in OpenSource where he experiences one of my only complaints against Open Source Software: User Documentation is Almost Always Out of Date.
I work to keep an eye on the latest and greatest things coming down the line. As a result, I've had the fun of working with some of the earliest public versions of Jakarta Tomcat, Apache Ant, SugarCRM, and of course, dotProject. All of these except SugarCRM suffered from the exact same problem. I believe the only reason SugarCRM differed was due to the fact that it was supported by a commercial company.
The development on all of these applications moves quickly and the bulk of involvement is in terms of development, not in terms of technical writing or UI designers. Therefore, it's incredibly difficult for first time users to jump into an application without some serious searching and hammering themselves. This has always been the case with early adopters, but it becoming more and more prevelant as the applications are becoming more and more common in both the development and regular consumer worlds.
As Satya mentions, this turns the standard communication channels on their heads. It's becoming less and less common for OSS groups to generate documentation. They're starting to move in the direction of community forums policed by some of the developers and a few dedicated users or towards a Wiki which allows for documentation to created, editted, and commented on by just about anyone.
Some may feel that this is akin to McDonald's requiring you to fill your own drink, but it provides many people an opportunity to contribute in ways not normally available. After all, this is how CaseySoftware got involved with dotProject.