I must just say thank you for sharing your thought processes and reasoning 
on this most interesting, and important, topic.

Just so there is no misunderstanding; As you point out, nobody is stopping 
me from using tags anyway I want but this is of course about making TW as 
useful as possible.

Ok, it remains a fact that in the end we still have a few practical 
problems with the current design that isn't ideal for more careless tagging:

   - There will be tiddlers that are difficult to find, as exemplified by 
   the tiddler Tagging <http://tiddlywiki.com/#Tagging> and someone curious 
   about how to use tags and therefore searches "tags". Note that this is an 
   example of a carefully designed and tagged tiddler.  
   - If we delegate ad hoc tags to be part of the text, we have a problem 
   when the tiddler is not really common text. An image, a rendered list, a 
   transcluded text where we might not ahead know if certain words appear, 
   etc. A technical solution to insert tags in the content anyway compromises 
   the resulting impression (this is not a small matter) and to demand 
   attention to if tags really appear in the text, if there in deed is text, 
   compromises the workflow for sure.
   - If we, hypothetically, limted tag to only be parent-child 
   relationships then people who use tags as more arbitrary labels must learn 
   that it is not OK to tag freely. 

Overall, I think TW currently is designed for an unnecessarily late stage 
in the brains tought process, not quite letting us take advante of the 
brains associative nature before we structure stuff mentally. If we really 
want TW to be *designed* to fit around your brain 
<http://tiddlywiki.com/#TiddlyWiki> I say we should tap into this - because 
we can and it would make TW an even more creative work environment.

I don't think I have much more to say on it right now so will put on, um, 
keep on, my thinking hat.

BTW, this made me remeber an actual project I had to give up on because of 
*other* limitations in tagging (TWC at that time) and this time with very 
structured tagging! It's really a funny case so I will detail it soon. It 
would be fantastic if it turns out I was just approaching it the wrong way.

@Astrid and particularly Mario and Tobias - great hearing your reasoning!

<:-)

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