I'm about to level my entire island and want thoughts from others who did it.

I really super recommend the Happy Island Designer!

I was pretty much like you, I wanted to completely redo my island. But in the end, because I pre-made my plan and (mostly) stuck to it, it turned out that there was a couple of acres of cliffs that didn't actually need to be removed, so I just left those bits and built the rest of the cliff up around them. It would have taken me a lot longer, had I gone in and flattened everything. :') It also allowed me to tweak my design a few times too, sort out the spacing a bit more etc.

I'm still in the process of making my island how I want it... mostly because it takes forever to move all the villager houses around. :p

Plan - yes.

I went full Godzilla on my island when I unlocked the tools and made a blank slate {no rivers, no cliffs). I didnt have a plan at first. Like yourself, I was building and adding little bits here and there trying to make it look good. It was frustrating at first because I’d spend 2-3 hours and decide ‘wait, this looks awful what am I doing with my life.’

This happened a few times because I didn’t have a general idea of what I wanted to do.

I started checking out what others had done for inspiration and a few ideas translated similarly into my island. After a looooooooottttt of work, it ended up going places I’m happy with.

TLDR; go for it if you have ideas in mind and have the time/patience to execute. I’d recommend saving a lot of bells/hook miles beforehand for quick construction of bridges, inclines, and PWPs.
 
It really depends on you as a "designer". I did it and I never could make it look right, so now I design around my island as is.
 
I flattened it based off the different levels the island has, except I tore down the entire 3rd level and made it apart of the 2nd. Honestly its a long and very tedious process, but its very helpful if you have no ideas/want to test builds since it's a blank canvas! I recommend moving buildings to the beach (as hideous as that may look) so you have nothing in your way while moving stuff around.
 
hi. I also did this. I didn't put much planning into it admittedly.

one thing I can definitely recommend is watching or listening to something while you do it, it's very arduous and will take a long time, especially if you want to go full-on like me and remove all trees, all rivers, all cliffs and all buildings.
but to answer your questions, I don't feel like I ruined my island! I can't say I've made massive progress since I did it, since I'm making sure to have a concrete plan and also I'm moving all buildings to the beach (which is painful as a non-tter). but I've removed all rivers and cliffs and I'm really happy with the first part I've finished, which is a lead-up to my museum. definitely needs more work but im happy with it atm at least

I will warn you when it comes to happy island designer: it's a great tool, but it's not perfect, only use it for a general idea of what you want. I say that because I made part of my plan, got started and realised the big section I planned would come waaayyyy closer to the town hall than it did on the island designer, despite me trying to follow it pretty diligently (I also made sure to properly map out my town hall on the grid). I'm going to try the method of screenshotting and drawing over my current map to give me a better idea of what I'm doing. I can't say I'm not at least a bit overwhelmed by the sheer amount of options I have to be honest

overall I'd totally recommend completely flattening your island to anyone interested, because it makes creativity and unique designs much easier. plus, even if you're not all that creative (like me) there is a lot of inspiration out there if you give it a good ol google.
of course, make sure you're completely sure before you do it because I have heard many people say they do believe they've ruined their island and have even had to reset because they were so unhappy with it lol
 
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