So I notieced that if I just paste HTML into the text box it all seems to format just fine and in some cases renders more closely to what i exepect than if I convert to markdown. My workflow is write in .org, export to (.md|.html), paste.
Not really, aside from Micro.blog and third-party clients usually defaults to Markdown. For example, if you use the Micro.blog editor and click the button to create a hyperlink, it outputs Markdown instead of HTML. So in a way, you’re going a bit “against the grain” by sticking to HTML only, but it’s not really an issue if you’re using an external text editor anyway.