Hmm, is is this best way to think of it? 
I think of it in terms of psychological locality.
こ - close me
そ - close to you
あ - close to neither of us
ど - unknown
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A better way to think of it than ‘we know’ is-
こ - In my space
そ - In your space
あ - In our space
ど - In whose space?
あ is not quite ‘close to neither of us’, it’s more ‘that place we both see/know’. It’s a symbolizer of shared knowledge, while ど is the symbolizer of lack of knowledge. That’s how I lump them into groups in any case.
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I have to think about this.
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どうだろう - probably whose space? how right? probably how…
help me with this one
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‘I wonder how’
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どう can be “What”, depending on the context. For example:
どうしよう？ What should I (we) do?
So I feel your pain. Out of all the こ、そ、あ、ど words , どう is the hardest IMO.
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One explanation was that it’s between ‘how’ and ‘what’ and there’s not really a direct translation into English.
That it’s a question word for an undefined action.
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English is the one to blame for being too complex. Japanese is doing you a favor by putting all the question words in one 
.
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A bit like the versatility of the f-word in English, noun, adjective, adverb and verb all in one expletive
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Except Japanese has the same thing going with やばい！lol
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Putting it all together: どうやばい？
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Pretty much! 
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You’re of course right with the “what”.
But I think this comes with translating する as “do”, which is the usual and normal translation.
But if you were the use the word “(re)act” instead of “do”, then you would use “how” instead of “what” in English as well.
I think this どうしよう often comes up in situations where one could ask “What should we do?” as well as “How should we react?”.
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After all this time, this was definitely a question I’ve been too embarrassed to ask at this point . Its one of those things that seems or ‘should’ be so simple, but whenever I think I have it, I get confused again with how its used in a new sentence.
Its interesting @jrmr50 that we seem to be a similar level and study time and you are having the same issue!
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Every time I use どうして or the variants I always seem to either have it in the wrong spot or say it in a very confusing way. so this particular grammar point I have a might sore spot for.
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The deeper I go, the more I realise my knowledge of the basics is lacking! I can usually bluff myself but occasionally I’ll have to read out loud /translate to someone, and I’ll get busted.
For some reason I struggle with translating だろう into (understandable) english, so どうだろう was a double whammy when I encountered it.
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Thank you for bringing up this topic. The discussion has been very helpful!
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I remember feeling like this when I was beginning japanese lol. Eventually all these kinda context words kinda clicked in my head and I get the meaning naturally now
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Oops found this in my draft’s folder a week later
I asked a Japanese friend, (what どうだろう means) and they said
“depends on how you use it”
“Well how would you use it?”
"Someone asks me if I am free tomorow and I answer “どうだろう”
“so it’s no?”
“not no, I’m unsure…”
“Like かもしらん？” [perhaps]
“Just so”
I think genki called “だろう the manly version of ね”- but I gave away my genki books to a 後輩
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