I often feel like the tech industry has a huge blind spot around "not doing things that make people hate you", and that conversations around tech tend not to factor "hate" (or 'resentment' if you prefer) into making things appealing.
For example I mostly hate Facebook for the choices they have made for years, and if I was ever going to stop hating them it would be after many years of sacrificial demonstration that they have a new philosophy in mind. Not unlike what it would take for a scumbag person to reverse my opinion of them -- candor and sacrifice, rather than nice words and promises.
It is not entirely impossible to stop being hated. Microsoft is occasionally managing it with VSCode and TypeScript, although I'd say I still 98% hate them; they have a lot to make up for, and Windows is still miserable garbage.
It is easy to become hated. Google is pulling it off remarkably. Making money is often easier if you do things people hate, although it's a short-term view -- it definitely increases short-term profitability and guarantees that in 20 years everyone will hate you and avoid you. But it's definitely economically rational for the company's employees, with their 2-10 year tenures and the metrics they have to hit.
Medium started as a breath of fresh air, and has become hated by being annoying. The point of switching from Medium is to screw over Medium, benefits be damned. If you're not factoring resentment into your utility calculation, of course this action won't make sense.