I'm a single-person operation for my small employer. I'm working on a couple of web applications that have grown to medium-size. We have backups going and everything is in version control with Subversion. I have comments in my code, but documentation outside of code is "spotty at best", and frequently things change.

What do I need to do to bring it to the next level, beyond a pile of ( version-controlled, well-commented ) code? What would you say is required to have a robust set of documentation outside of the codebase itself, where the project is at, and where it's going?

Ideally I would like some integrated system that would go from brainstorm, to requirements, to tracking bugs and features in svn check-in messages, to documentation. Would trac or redmine do something like this? I would like to show to my boss, "This is the prioritized list of features, this is where we are now, this is how long I spend on this feature, how long I spent on this bug" and I'd like to spend the minimum amount of time managing the projects :)

What about ERD and UML diagrams? Is a project incomplete without them?