I'm kind of in re-boot hell myself right now, but I have 0 regrets.
I had 8 chapters of my comic in black and white, written right-to-left, and littered with so many problems I can't re-read it without cringing.
But this story is my baby. I want to finish it (Even if it's gonna take years). I want it to be the best it can be. I did so many re-do's and take backs in the original version that it was such a jumbled mess (Like for example, I revealed a character and then decided "nvm it's too early for that" and went and edited a whole chapter to not reveal this character yet, but it was such a jumbled mess where sometimes people were finding the version where they were revealed and sometimes they weren't).
So from that point of view...should I have just continued the comic with all those old mistakes and styles intact? In myyyy opinion, no. It would have been such a jarring and jumbled mess for readers. I'm aware styles change and the beginning of a webcomic may look completely different from the end, but completely switching the reading format would have been a bit to extreme in my opinion.
On top of that, this started as a dinky little comic I started in high school. Since then, I've gone to school for art and learned a lot more than I knew back then about story and art, in addition to learning from a lot of mistakes from my last version (Not to say there aren't mistakes in this version too).
So that said, should I have just started a new project? I do have other stories I want to tell some day after all.
In my opinion...maybe, but in this particular case, hell nah. I love my story and characters. I don't want to abandon them until their story is told, even if it means taking another try at telling it. I don't have a TON of readers left over from the old version of my comic, but to them I do feel sorry that they're having to wait so long to see some real new content, but in the end it's for the better of this story. And even though I am rebooting the same comic, they ARE getting some new stuff. New scenes that weren't in the old version that benefit the story, things moved around, and of course just new colorful pages in a much easier to read format (Not to say black and white can't be gorgeous, but I prefer my own story in color). My few readers that have stuck around since the original version all seem to be very supportive of the reboot.
And THAT said, I'll give you another example of an experience I've had:
I did have one comic before my current one. It was semi-successful and had a decent readership, but in the end I decided to drop it for my current comic. And BOY WERE SOME PEOPLE PISSED. I'm sure they would have much rather preferred a reboot of that story than this new thing I had started.
I still don't have any regrets stopping that comic though. I still love the story and would love to go back to it some day, but for now, that one is a case of "let sleeping dogs lie." Maybe some day it'll get its own reboot as well. But why did I feel okay with calling it quits for now on that comic and not my current one?
Eeh, well I guess it's really just where your passions lie. If you really love your story and want it to be told the best of your ability and really think you can do it better than did at the beginning, I say go for it. But take some time. If you REALLY think your comic needs rebooting, those aren't plans or changes you can figure out in a week. I had one or two years in between my old comic and the reboot. I'm sure the time varies for everyone, but this sort of gave me enough time to make a much stronger story and art than I original had and was also long enough that readers were excited for any new content, even if was a reboot.
If people really love your story, they'll be excited whether it's a continuation or reboot. Think about all the reboots of cartoons lately. Granted, a lot of them have been let downs, but fans were STOKED for the Powerpuff Girls and Sailor Moon reboots (Just please do your story better justice than these did).
I know there's a Samurai Jack reboot coming up as well, and I'm actually not sure if it's a reboot or a continuation of the old show. But either way I am PUMPED! I don't care! I love Samurai Jack! I'm ready to see it again whether it's starting over or continuing!
I think comics are the same way. If readers really love your comic, they'll be excited no matter what. But just give it enough time for you to actually make the improvements and just long enough that readers still remember you and are excited when you come back.
HOO BOY! Sorry for rambling quite a bit! I hope that wasn't too wordy... :'D