I keep getting asked to support writing rich-text-formatted posts in #Hometown (we already read them just fine). I finally wrote down, in this comment on this Github issue, a short essay outlining all my concerns with doing so:
https://github.com/hometown-fork/hometown/issues/1274#issuecomment-1379647384
Some of this is problems with Markdown, while some of this is problems with interoperability regarding any rich text rendering at all.
@darius really great thoughts, and honestly a frustrating example of how the general accessibility of markdown just wouldn’t work out, and could ultimately make things less accessible with key context vanishing unpredictably for users on other servers :(