Re: Re writing

#2
No one can make this decision for you. You either choose to rewrite it or you don't.

Consider why you want to rewrite your story and what your goals are. Are you writing for fun or to improve/chase a career?

If you're just writing for fun, do what would make you happiest. If that's starting from scratch, go for it. No one has the right to judge you for that, it's your hobby. Own it.

If you're wanting to improve, rewriting the first 10k of your story over and over won't help you. You can take what you've learned and finish your story, improving as you go on. No one starts as a perfect writer. Most people don't even start as good writers. The more you write, ask for feedback on, act upon given feedback (or learn which feedback to ignore!), the better you'll get and the more confident (hopefully) that you'll feel.

You do you.

Re: Re writing

#3
It depends on the amount of work you want to do and how it *feels* for you!

To gauge, I'd take a good hard look at your first chapter. How much work will it take (in your eyes?) Changing a word here or there? Rearranging a few sentences? If it's mostly just "editing", it can be a slow process sometimes, but well worth the effort to bring something you love to the next level. 

If literally the only think you like it about it anymore is the context, rather than the content, and it takes entire paragraphs of rework because you've grown so much, that's a bigger decision (and also huge growth, so congrats, if that's the case!). Sometimes people find it more refreshing and motivating to just let it lay where it is and start something totally new with your new inspiration and skills. 

If you really love the story and just know you can tell it better a different way, you can instead build a new outline from the old story. Go through the chapters and make bullet points of the sequence of events and particular quotes or visuals worth saving, then take a whole new run at it on a blank doc, start to finish, letting go of the old prose completely. It will be a lot more liberating and less stressful than working inside the confines of something that already feels like it's not working. That can be tiring and frustrating. <3

It's really for you to judge. It's about finding what feels good, and if the rewrite-work feels like drudgery it can suck the joy right out of it. You don't have to let that happen!

Re: Re writing

#4
If you've already re-written it once before, then I'd say it's time to complete the story and start the next one. I'm saying this as someone who spent far too long noodling on a single property. It's a trap that I hope other people can avoid. You improve most by putting what you've learned into your next story (there've actually been studies on this).

This is also one of the hardest things to do. We put a lot into our stories. They're significant and meaningful to us, regardless of their quality. But one of the hardest things to learn is to be a little less precious about your own work. It's a fallacy to believe that you've only got a limited number of stories in you. You have infinite. You can make more... and you should.