I've been a Bootstrap user for a long time, but I recently made the jump to Tailwind. It's not the revolutionary upgrade I was hoping for, but it's nice evolutionary step in the right direction. It's quite intuitive, but it doesn't get rid of most of the frustrations that come from doing layouts, as those come from the design of CSS itself. `@apply` makes the upgrade worth it though, it's easy to make custom classes from the Tailwind elements.
The one thing I don't like is that the culture around Tailwind seems a lot more proprietary, like you're getting three quarters of a product that you need to buy the rest of, whereas Bootstrap felt like you got everything you could ever need for free.