I am currently rebooting a 5/6 year old story of mine. I planned out about 20+ chapters at the time, but due to my lack of skill in both writing and drawing, the pages i did create were lacking.
I plan on not just rebooting, but reworking the story.
Personally I think a reboot should only be done if the creator has not already started creating the pages of the story or only has a few pages created.
Plan the story first and make sure it's solid before starting to draw your pages. It's always easier to rework the story if it has plot holes or redesign characters as you work on the story in the development stage, but once you start to publish your pages, that's it, you are stuck with what you've got. Make sure you feel comfortable with your story before you start creating.
If you are rebooting because you don't like your art, keep creating, your art will improve by working on pages of your comic.
But do make sure you practice drawing your characters/ world beforehand. Some little changes you might make as you start drawing the comic can be avoided by planning beforehand.
Better to avoid rebooting in the first place by properly planning out your story, lore, world and characters first.
I learned this the hard way.