Cracks knuckles. Okay, this is something I can definitely give input on, considering my entire comic is a reboot.
I think reboots are fine under the right circumstances. I started the original version of my comic in high school, in the middle of a weeaboo phase. It was over 200 pages of a hideous, poorly paced, read right to left, mess.
I had edited and redone so many things so many times, that the dwindling readers I still had were just completely lost. The art was horrible and the entire thing was read right to left.
And then I went to art school and my art improved a ton from high school, as did my story telling skills. I'm not saying they're the best in the world, but they're certainly far higher than my limits in high school. This is a story I want to tell, and there was no point in trying to salvage what I made in high school. I had maybe 50 active readers at most and a story that was stitched together in a format that nobody wanted to read (the entire thing was right to left). What was the point of continuing that?
A reboot was absolutely necessary for my comic. Pages went from this:
to this:
(Btw, not every page is a remake. There's about as much new content as remakes.)
The story was fixed. Pacing was reconsidered. Plot holes were filled. Parts of the story were moved around for better flow and less confusion. Designs were changed to far more appealing designs.
I went from having maybe 50 active readers on DeviantArt to having 1000 by my 2nd chapter. Most likely because I got a staff pick. Which just kind of leads me to another point...
There's no way THIS, the original opening to my comic, would have gotten a staff pick, if I had started to upload to Tapastic with the comic in its original state:
Versus it's new opening:
So to sort of sum up... I think reboots are great and absolutely necessary...when you're ACTUALLY rebooting. I DO see a lot of people doing what you're talking about, where nothing really changes. The art stays about the same, maybe they just add color, the story is only slightly tweaked, and you continue to see the same mistakes. I think if you're gonna do a reboot, take a lot of time. I had about 3 years of art school in between the old version of my comic and the start of my current one. You aren't gonna improve enough in one measly month to make the time you waste on that reboot worth it. If you're gonna reboot, make sure you are actually going to make a better product.