Balance between precision and simplicity
That may be suggesting a cardinal sin in philosophical writing, but I'm hopeful you will understand, because you said something about writing poetry.
In the same way that metre and rhyming in poetry forces you to have a more complex relationship with natural grammar than you might otherwise have, just so, a "conversational tone", or any other improvement to textual digestibility, will necessarily have an impact on how you present your arguments.
As an exercise, try taking a page of your writing, with all of your "hedging" and context and examples. (You illustrate with examples, right?) Now try writing the same thing in a quarter of a page or less. And keep the illustrative examples. Something has to be left out, or at least folded in more tightly. Good poetry sounds more natural after a great deal of folding and polishing of the thoughts and language; this is true of other writing as well.
As a natural windbag and hedger, I've had a front row seat observing how people get lost in my digressions into qualifying what I'm trying to say. More words can actually communicate less, if you can't hold someone's attention.
I'm not saying that all digressions are bad; "color", and organic presentation, and circling back to tie things together, are all wonderful and persuasive techniques in writing. It can even be good to imagine a person who you're explaining something to - and to write down your arguments or points as if you were walking that particular person through your reasoning. (That might even be the real answer you're looking for.) But remember that, unlike your imaginary audience, a real audience will have a limited amount of patience as they're waiting for you to get to the point. Make sure your writing is clear and simple enough, and gets to a point.