Yep. I'm hopeful that someone will inevitably turn up in the comments and reveal a great way to do it but everything I've seem is just janky and awkward.

I've basically stopped using my static site as a result of media management being a pain. I'm probably going to do back to Wordpress or something (shock horror!). Wordpress isn't hard to manage at all quite frankly, it's just a different set of compromises compared to a static site. It's also super easy to manage rich media and as I'm falling squarely on the side of 'get shit done' it's looking like a good option.

It's trivial to cache it well and update it. Yeah it's not as secure but there's a risk vs usability judgement that has to be made. And I think I'd prefer to be producing content and having some good backups rather than just not use my site.

Check out HardyPress. They host WordPress in an anonymous environment that goes to “sleep” when you're not using it. A static version of the site is deployed to a CDN when you're ready to publish changes. It's been the best of both worlds for us.

https://www.hardypress.com/

If you’re not against PHP and hosting PHP code, as mentioned in the OP my go-to tool would be Kirby. The mix of static content and a powerful content API is the sweet spot for me, when I don’t absolutely need static HTML. It does require a paid licence though (note: I’m not affiliated with Kirby or its developers).

I'm just looking through now. It does look pretty good. I'll have to play with it and see if it falls in the right spot between 'I'm too lazy, just point and click' and wanting something lighter-weight and easier to reason about.

This may be the comment you've been waiting for! I implemented Wordpress API compatibility on top of a static site service.

Send me an email at [email protected] to try the service.

Forestry.io is a CMS for static sites that includes a media management interface you might like[0].

We also support uploading images to Cloudinary instead of committing them to your git repo to prevent repo bloat.

Depending on what you're trying to do, a non-CMS option that will remove some of the tedium of inserting all these images is to take advantage of Hugo's Page Bundles feature[1]. With this you could just group a bunch of images in a folder and iterate over them in your templates.

[0] https://forestry.io/docs/editing/media-library/

[1] https://gohugo.io/content-management/page-bundles/

Give Ghost a try (https://ghost.org/). They have, I believe, potential to eventually add static site generation. There's an open issue about it, I really hope it happens.

I agree with you that sitegen from git is just too cumbersome when the articles aren't very bare/simple. Also when there are multiple users contributing, especially non-technical users.

Ghost is expensive. Actually it's incredibly expensive when compared to the competition feature wise.

It's also a pain to self-host (especially compared to competition seeing as it's basically a requirement to go for a full VPS install) and is pretty opaque when anything goes wrong.

It's easy to use and slick, and I'm not OP, but it's not for me at least.

If memory isn't playing tricks on me, you can go to staticgen and in the language pick bash. There was a sweet one developed with photos as front runner. It may or may not be what you are looking for.