You can find other platforms we're updating is a lot easier.
That is the issue.
- 2 major versions and 4 years out of date.
- Upgrade started as a half-hearted "in your free time" effort with no official team, or maybe 1 dev (article says both).
- Upgrade included "cleaning up technical debt and improving the codebase", (you could define almost any work under that umbrella).
- At the end there were only 4 devs full-time on the upgrade.
I don't know of any platform that would make the above situation all that much easier...
Care to name the platforms that would be much easer to update at Github's size across two major versions?
Rails was hugely popular for years (and still is, in a lot of ways). There are countless articles about it and it's been for a ton of projects. There are a lot of internal Rails apps built on earlier versions that are owned by companies with either limited in-house development resources, or none at all; in which case, it's easy for decision-makers on the business side to push off updates (assuming they even know about them). "That doesn't sound like a big deal, we'll just do it for the next one." A bit of time passes, and then you're two major releases behind and you're looking at a serious effort. Or maybe it's developers who make that decision for what are likely valid reasons in the short-term. Upgrades across multiple major releases aren't exactly uncommon because of that, and there are a lot of articles detailing them, blog posts discussing or complaining about them, questions on SO, etc. as a result.
For the most part, though, I don't that that Ruby or RoR is uniquely difficult to upgrade compared to other frameworks. I've handled upgrades across versions that have gone ridiculously smoothly, and some not so smoothly.