A markdown-based blog lets you preview, if you're typing into an editor that supports previewing markdown. I do my long-form writing in LibreOffice Writer (because Fedora), then the "blogging"/translating bit in PyCharm in a markdown file. PyCharm has a rich markdown previewer, so I can write short posts in it, without the translation step.
I'm not personally aware of a static site generator that supports drag-and-drop images, but nothing stops such an extension/plugin from existing. When I want to embed an image on my site, it goes into an /images/[year]/ folder and is referenced in the markdown file with the manually-typed partial URL, as you mentioned.
My blog uses many custom features not found in plain markdown so a simple markdown preview found in some editors isn't helpful for verifying the post will work correctly.
> I lost the ability to preview.
Not really. You can keep the local server running and a browser window open. The server can be configured to regenerate the site as changes are made. Simply refresh the page to see your changes.
I have many machines I work from. So no that won't work as easy as a non-static site. Wordpress I can edit and post from my phone. Can't run the static site generator on my phone
Adding images into a post was also nicer. Just drag and drop instead of copy into folder, check into git, manaully type urls like it is now.
I use a private repo on github so at least I can add something without having to be at my computer but still no preview or nice UI.
Any static generators have well designed solutions for this?