[[:Category:User Guides]]...good idea or bad?

My concern with this is, will all guides on the same subject share a page? Or will they be subpages to each persons' user page? If it's all on one page, we could separate them by header/editor, but then some may get outdated if the editor stops contributing to the wiki and other are not allowed to edit others content so we would have to first think of a basic rule set for etiquette.

No. I'd rather have it kept in separate pages and yes, they will have to be subpage(s) of the user just as a way to know who wrote it and such. Fortunately, I am fine with anyone editing and correcting my mistakes, provided there was a given reason and I approve of it. I'll leave it up to the user if they want people editing their page(s) or not.

Of course, the title will have to be straight forward in order to make finding the guide much easier. I mean "Finale Guide" could mean anything unless someone puts like "G1 Finale" or something like that. Same thing with stuff like guides to skill sets. The name of the guide will have to be something simple and short, but still reflect the guide's content.

Lexis covered the rest of your concerns, but on the topic of being outdated, we may need to add an exception to the current rules of userspaces to allow others to deprecate out of date guides. Perhaps that should be reserved only for staff, and others would have to report it to them? I'm not sure such a measure is necessary, though. I trust the greater amount of you to not be trolls about the system.