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.![]()
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.