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Hugo can handle images through its asset pipelines, so you should be able to just store them with your markdown. I agree it's a little more friction than a blogging pkatform, but it does mean that you can just write your posts in your editor of choice and publish them with just a command, or if you're feeling fancy, set up git to trigger publishing when you push.
This is a good point actually. As others have mentioned, editors like VS Code make working with images in markdown easier. I'm also looking into Obsidian, which I already use on my phone, but it might be too much effort to setup for this purpose.
So I'm warming up to the idea of using a static site generator, just need to figure out a workflow. There is also Zola which is kind of like Hugo but smaller and written in Rust.
Hugo is really easy to automate too. Just toss it on a github/codeberg repo and use one of the community's publish pipelines.