Many times. The "best" way depends on what you've got and what you want. Some people will ask users to label pages, others will simply delete, others re-arrange and then delete after a while. Some people will go after add-ons and macros as part of a "clean up", some will kill off old attachments, others will focus entirely on pages.
I'm afraid there's no simple answer for "best way to clean", as it really does depend on what you want to get out of it.
Big thanks Nic...
"best" way to us is to design a way where we can create a new structure...and then put our existing content that is not well organized now into the new structure that we've created.
In my mind...having two completely separate instances would really do the trick. But the challenge with that is that I'm not sure it would be easy to move pages, content, etc from one environment to the other.
Gotta be some tools out there to help with this?
I'd be tempted to do that in the same Confluence, but creating new spaces for the content. You'll find it easier because you can move the content you want to keep into the new structure directly, rather than having to fiddle with export and import across two instances.
I don't know that there are any tools that could help you - your describe housekeeping is simply moving things around - a human needs to decide what to move and where, and once you think you've got everything, just delete the old spaces.
What you need is a technical writer and/or knowledge management specialist - managing the content of a wiki, whether it be Confluence or another type, needs a good understanding of taxonomy design, archival strategy, user needs, and so on. Being technically adept with Confluence will help a person understand the tool and the options, but that is a supplement to the skill of a documentation/knowledge specialist, not a replacement for it.
It's also not a one-off approach, as without ongoing content management your Confluence will quickly become un-organised and overstuffed again. This is a job for your documentation people to manage over the months and years. The current term in vogue is "content curation", i.e. managing the content and surfacing the most useful elements, whilst making it easy for people to find the "long tail" of things which are less often required. But whatever you call it, once you've front loaded the pain of sorting it, you need to have a plan in place to manage it as you go forward (and people to implement that plan as their primary job responsibility).
(Caveat: I'm a documentation and knowledge management consultant who helps companies do things like this, so make of my comments what you will )
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