Post History

The order in which the reader sees it is not necessarily the order in which the author wrote it.  You can use this to get past rewrite loops or other blockers.

When writing (both fiction and non-fiction), I sometimes insert "placeholders" -- I'm going to need a scene or section here that does X, Y, and Z, and I'll come back to it later.  (Use any consistent convention that will let you find them, like "TODO:" or square brackets or anything else that won't be in your actual writing.)

You already have an outline and it sounds like you're still finding your authorial voice, so instead of rewriting the first section over and over, I recommend picking some other part from your outline, writing or rewriting *that* with an eye to how it fits into what comes before and after, and iterating.  After you've written or rewritten a few *different* sections, you should develop a better feel for the style and voice you want.  Consider adding datestamps to sections of your manuscript so you'll later be able to answer the question "which parts should I look at again after deciding that *this* section is the style I want?".

Years ago, and over several years, I wrote an in-character journal for a game I was playing in.  My authorial voice changed a *lot* from [my first game entry](https://ralph-dnd.dreamwidth.org/3130.html) (and the [prequel](https://ralph-dnd.dreamwidth.org/2839.html)) to the [last](https://ralph-dnd.dreamwidth.org/33668.html) [few](https://ralph-dnd.dreamwidth.org/33941.html) [entries](https://ralph-dnd.dreamwidth.org/34057.html) (uh, spoiler alert :-) ).  If I were going to revise that with an eye toward creating a novel with a cohesive voice, I think I would start in the middle and work toward both ends.  The largest changes would be in the earliest parts, and if I focus on those first, I might find myself thrashing and never get to the rest.  I, like you, already have the pieces and an order; we can use that.