Eventually I was tasked with upgrading it to Drupal 8/9 (a new generation, with no backward compatibility with 7.x). It was basically a full rewrite. Well, I built a prototype in the new version, but it was still a convoluted mess -- slightly better, but nowhere near "modern". The whole thing is just way more complicated than it needs to be, and reminds me of 90s-style data management, and a web UI reminiscent of cheap wifi router dashboards: ugly, very slow (much of it wasn't ajax yet), and in general just total drudgery to work with.
After I built that prototype, I swore to myself, "This is the last time I'll ever use Drupal. Ugh." As a proof of concept, I also built that same prototype in several other CMSes: Wordpress with Advanced Custom Fields, Ghost, DatoCMS, Strapi, Contentful, GraphCMS (now Hygraph), Storyblok, Grav, etc. ALL of them were way more usable than Drupal, and each one took like 1/10th the time or less to make. It was especially fast with the headless CMSes + Next.js
Wordpress with ACF was probably the closest direct comparison, and that provided a much better editor experience, but still had poor DX (cuz you had to either work in Wordpress/PHP, or else shim ACF with other plugins to make it act headlessly).
It took me a few months to upsell the team, IT, and management to switch to a proper headless CMS instead, completely detaching the editor experience (managed by the CMS) and the DX (we were now free to develop the frontend however we wanted to, fetching content via GraphQL). It made everyone happier in the end, and it's much more maintainable.
Editors never have to care about forced upgrades, web technology changes, etc., anymore, and devs don't have to worry about accidentally breaking the editor experience while working. And a modern Jamstack (or anything else, really) is way way easier to work in than Drupal or Wordpress templates, especially since they don't share the same server as the database & editor and can be independently hosted, developed, tested, deployed, etc.
I still would never touch Drupal again. I've never used a technology I was so annoyed by (and that's coming from someone who grew up writing AT commands for their 14.4k modem, made websites in Perl, had to use Applescript to shim Filemaker into a web CMS... ugh.) Drupal is by far the most traumatic software I've ever had to use.
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Side note: Drupal itself aside, companies like Acquia and Pantheon do make the experience much nicer though. They basically manage hosting, forking, dev environments, backups, visual diffing etc. for you, like a bespoke cloud tailor-made for Drupal and Wordpress. I would definitely host at one of those companies (I prefer Pantheon, personally, but both are great compared to non-Drupal-specific hosting).