It's likely that some others here have followed along with the old Flash based Lena tutorials at some point. Are there any modern resources in a similar vein? What I found fulfilling about them was that some (all?) sections talked you through reversing/keygenning actual applications, rather than simple CrackMes.

I know there are projects from OWASP etc with a realistic site for learning web security, but I don't know any realistic installed software for teaching in the same style with multiple targets in the same package.