I don't believe Hazel will solve that last issue, but I may be off about that and you're certainly more skilled than I am.
>When you say keywords, are you just referring to using certain... well keywords... in the filenames?
Keywords are not in the file name, they're embedded in a file's metadata. For example, do a Print to PDF of a web page, but in the last dialog where you can save, note there's a Keyword field. Add something there that's unique, then search on it with Spotlight. Have lots of Keywords in use? Then Spotlight can use a keyword:[search term] search, similar to how there are many other built-in search queries.
My primary setup is to have Hazel monitor specific files in specific folders looking for specific content within those files. Based on the results, Hazel runs my Automator Actions to embed the Keywords I want (especially helpful for organizing my business files, but I have plenty of other uses, like Hazel filing documents based on the Keywords I added when using Print to PDF).
Ultimately, it sounds like you have a solid system accomplishing most of what you want done. Certainly no need to redo a viable setup. I was just hoping Hazel could help with the Pages files, and maybe secondarily some other parts of your process.