Things That Danny Tries To Keep Asking Himself:
Can this content be stored as structured data, so that manipulating it and displaying it can be done in a controlled and programmatic way?
Can this activity or process (virtual or phsyical) be generalized into a function that is written once and called multiple times?
Can this display of output be described as a system of rules, so that new content for the output doesn't have to be formatted by hand?
Is the data as independent of the presentation method as possible?
How can this be made modular instead of monolithic?
Have you investigated whether a system can be automated, and if there are readily available tools for doing so?
If the problem seems insurmountable, or if the solution requires more than 3 - 5 people to change their worldview and habits in a hurry, are you sure that you're even asking the right questions?
Can a prototype solution be pieced to together from existing tech?