Got to be honest - if it wasn't for Scrivener 2 I'd still be on Windows. And given how crappy Word for Mac is I have no doubt I will be doing the final revise back there. Microsoft say Mac Outlook is 'on a par' with the Windows one. They're clearly delusional. Try Mailplane though - it only works if you're online I think but it's very good.

PS. Your working method is even weirder than mine.