My experience (and the experience of thousands of others) is that in practice, an approach like Tailwind is much more maintainable, even if it's superficially ugly.
At the end of the day it's a lot easier to understand what's happening in a template where you can see all of the styles directly attached to each node instead of having to map things together in your head across multiple files.
For example, for me at least I can't believe how much more difficult it is to look at your average CodePen demo and understand what is doing what at a glance vs. looking at a Tailwind template. With traditional CSS there is just _so_ much indirection in comparison.
At the end of the day it's a lot easier to understand what's happening in a template where you can see all of the styles directly attached to each node instead of having to map things together in your head across multiple files.
For example, for me at least I can't believe how much more difficult it is to look at your average CodePen demo and understand what is doing what at a glance vs. looking at a Tailwind template. With traditional CSS there is just _so_ much indirection in comparison.