That's the majority Hacker News kind of opinion "Sales or the CEO fucked it up for the engineers" but another likely explanation is that the main source of frustration (forced updates for everyone) came from the engineering side because most developers hate maintaining older versions. Then someone said "you can't do that to enterprise customers, they demand to pick their own versions" which resulted in this button for the paid version.
This is a desktop app, so there's no need for engineering to maintain older versions. They can just ask users to upgrade to the latest before opening support inquiries. They can even deprecate old web endpoints if they want, and again ask users to upgrade to continue using.
I'm agreeing with you here for the first part: that's another great well-meaning dev explanation.
The ball-dropping is sales/product/leadership not being aligned on user advocacy. "Our velocity & sales > breaking user environments" means either the former is overly prioritized, or the people making decisions are too far from users (developers) to understand their daily needs. Managing docker versions for dev/prod drift isn't "1% of devs 99% of the time" but "99% of devs 1% of the time", so it's a real miss.
In an alternate org where the user advocates lead might look more like:
* <reject early on the current feature plan proposal as user hostile and instead...>
* free: default to auto-update (or not)
* free: flip
* pay ("Pro"): one-click to switch to another version, both forwards & backwards
* pay ("Enterprise"): centrally managed update schedule, version tracking, audit logs, etc. for all devs in your org
Folks there are some of the best, so I'm sure most of this was considered, and thus it's an org/process problem
