Earlier quoted context omitted.
Technology choices, and life's choices in general are like a spectrogram of different wavelengths with positive and negative values... Like "this will help you today, but bite you in the rear tomorrow", or "this will help you tomorrow, but be annoying today". And it also varies by different conditional developments, if this happens, if that happens, can you implement a change, or the solution is "write-only" and so o…
What makes you think tailwind would be hell in the future though? It's just a load of classes on html elements. Maintenance is pretty easy. I do agree with you on the headline though, of course tailwind hasn't won anything!
If you have a very simple page this doesn't matter, but as your site/business grows, it does.
Second, Tailwind obviously promotes a ton of repetition in the same way that using presentational attributes from the 90s and style="" does. This not only adds, again, burden to the CSS engine and DOM, but this "ease of copy pasting" that the author boasts about in the linked blog means you can easily end up with tons of subtle or not so subtle inconsistencies in your site's code and components, UI.
Copy pasting is easy. But there's a reason why we define classes, functions, modules, and reuse them, instead of copy-pasting our code everywhere. Copy pasting is a strategy for a quick start and a very short journey as you paste more and more variations of what you're trying to do around your site. Now change them all consistently. Oh shit, I guess... find/replace + regex? This works sometimes, but it's a deeply unserious approach to change management in an application/site at scale, and means your velocity and quality both will suffer.
I'm aware of the way to define custom classes as sort of "components" in Tailwind, but at this point... you're literally using Tailwind as you would CSS, but with a ton of indirection, gibberish, and very very unclear precedence/specificity rules.
You will also get many people complaining about compilation speed for larger sites. A problem that is quite bizarre to have for styling with a language that doesn't require compilation when you use it in a sane way (and SASS etc. are extremely fast and don't have this problem, there's even a Rust SASS parser I believe, that's even faster).
Tailwind also severely restricts your precision and expression. I probably don't have to explain the limitations of inline styles when those styles have to change from user interaction, or for different devices, and container size and so on. Tailwind makes all this extremely bizarre, if it addresses it at all. In "plain" CSS (and other more reasonable tools like SASS), it's trivial.