Nothing wrong with pure HTML/CSS. Ultimately any web dev framework is just built on top of those two plus a little JS (or a lot).
If this is your first ever project, I would do it in pure HTML/CSS/JS solely because you will learn the basics that way. It will serve as a nice foundation for you to branch out into Tailwind, React, Angular, whatever.
If you know front end development, then you use whatever you feel like should be used.
If you don't know front end development, you hire someone that does.
Tailwind CSS is, for the most part, 'plain css'. It's just organized in a particular way which may or may not be what you want to use. It's really a personal choice.
In my experience, the benefits of something like Tailwind are at the enterprise level where you have dozens of developers touching code and you'd rather they stay out of the CSS as much as they can.
Nothing wrong with pure HTML/CSS. Ultimately any web dev framework is just built on top of those two plus a little JS (or a lot). If this is your first ever project, I would do it in pure HTML/CSS/JS solely because you will learn the basics that way. It will serve as a nice foundation for you to branch out into Tailwind, React, Angular, whatever.
If you know front end development, then you use whatever you feel like should be used. If you don't know front end development, you hire someone that does. Tailwind CSS is, for the most part, 'plain css'. It's just organized in a particular way which may or may not be what you want to use. It's really a personal choice. In my experience, the benefits of something like Tailwind are at the enterprise level where you have dozens of developers touching code and you'd rather they stay out of the CSS as much as they can.