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I can't say much more than what the title already tells you I'm only writing this while getting frustrated during a style maintenance session, because that's when, and only then, Tailwind becomes a nightmare.

Using Tailwind makes development incredibly fast, and these days even more so with component libraries like Shadcn. Same goes for AI it's way easier since the number of files to read and write is cut in half.

The truth is, nobody wants to spend a single extra minute writing CSS to keep things tidy and clean, especially when you don't even know if the project is going to be successful. So let's iterate faster with Tailwind and don't get me wrong, I'm the first one to take this approach. At the same time though, I know what a nightmare it becomes when, six months later, you have to go back and maintain or fix any style. If you say you can read a whole component with all its Tailwind classes and have no problem with it, you have a superpower, dude. And it's not just that what about when you're trying to go from the browser to your code, looking for a specific component? You'd inspect the page, click on that element, copy the class name, and pray you're the only component using that Tailwind class. With CSS, that same search is a confirmed headshot.

We have a saying in Spain that perfectly defines what Tailwind is: "Pan pa hoy, hambre pa mañana" bread today, hunger tomorrow.

The good thing is, now with AI you can debug it way more easily. That's also part of why I keep using Tailwind.

Conclusion

Use whatever makes you feel comfortable, and be aware of your time and capabilities. If you ask me, I'd keep using Tailwind for its fast development, trade-off maintenance nightmare included. There is one case where I'd go for pure CSS though if I have a project where I know from the start it'll last for years, with many other people working on it and a real guarantee of long-term success. But for now, since I never know when a project will actually take off, I'm going to keep using Tailwind. Sadly.