I found that Hugo requires a shift in asset organization in the sense that assets are collocated with posts. If your post has three images, those images are in the same directory as the post markdown.

Jekyll keeps assets separated. Your posts live in _posts. Your static assets live together in a different directory.

I briefly experimented with switching from Jekyll to Hugo, but had too much invested—custom plugins and reliance on existing Jekyll plugins—in the Jekyll ecosystem to make the switch worthwhile.