@noah-cochran Have you tried using the Google Docs dictation tool? It’s way better out of the box than the last version of Dragon I tried was after hours of calibration. The main problem comes from saying constructed words or names, but generally it does a fantastic job.
I get a lot of structural feedback as I write, so I make whatever big picture changes I need to (when I get the feedback in time) before finishing the first draft. After the first draft is finished, I decide if I need to make any further structural changes, then go scene by scene through the story using ProWritingAid and a checklist I’ve built over time.
My goal is to create a story that’s good enough, not one that’s perfect, because I know I’ll grow faster by learning from mistakes on finished products than polishing the same story for three years (which I’ve also done).
To give a concrete answer, I don’t rewrite an entire draft, and I usually only make one round of edits after making my first draft fairly clean.
"...the one with whom he so sought to talk has already interceded for him." -The Master and Margarita