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How do I know when I should rewrite vs. editing my first chapter 

A little context for my question...

A long time a go, I started writing little vignettes for a character I was playing in an RPG group.

The vignettes ended up joining up and becoming sort of a backstory/first chapter for the character but because of how I stated writing it wasn't as coherent as I wanted and left me with too much to change, so I wrote an outline based on this rough draft and started to rewrite the story.

But I found myself having to write previous scenes to prevent awkward exposition (e.g. they main character started out on a mountain, but I found it easier to write the scene before that explaining why they were on a mountain).

I scrapped that, and I've started afresh (what was rewrite two) with what feels like the earliest relevant moment I needed to capture.

Because I understand the story and character better, this first scene was much longer and in my opinion better written than my previous attempts. However I reached a point where I wasn't sure how to proceed took a break.

In this break I managed to read some novels, something which I'd been struggling to focus on at all for several years, and this inspired me to change tact with my own story.

I came back to try and make more progress on the first chapter, but working with that text and trying to push the scene on felt awkward as it no longer matches the vibe/voice of the story I wanted to carry on with.

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In summary, I've been favouring rewrites over editing while finding my style, and I'm worried that I'm going to keep rewriting and not actually progressing my story.

I'm still very new to fictional writing, I'm struggling to find what's normal and natural in process.

How do I know when to re-write Vs edit my first chapter to get the right feel for the story?