What do you mean with "best writer"? One could argue that no writer is better than another, there is just people with different tastes.
In terms of popular impact, SSC obviously wins. However among "insiders" there are always implicitly lauded favorites. Is it about the general capacity to convey complex topics succinctly, general "immersion" in the writing and ability to consistently foster a compelling mind-space via the imagery and ideas handled in the text, etc?
This is just me being a curious outsider. Interestingly I often peer into insular communities and find that there's often an unsaid tapestry of implicit assumptions and customs. All that I've discovered so far is that SSC is the darling favorite, Yud is liked but also made fun of for his behavior and more blunt approach, and Gwern is liked but not as notable, though imo he has the best website.
Is the best way to peer into these ideas via a prolonged investigative type outside observation, or should one feel only a worthy potential to fit in to the common character of the crowd if they can take a short peek at the general shape of the culture and immediately "get it"?