I just finished migrating App-o-Mat from Bootstrap to Tailwind. Here are some things I recommend if you are trying something similar

1. Don’t try to keep the same markup. It’s likely you can make it a lot simpler.
2. If you need icons, use Heroicons.
3. If you use @apply, use it to style tags or to make more utilities.
4. Generally, Tailwind seems mature enough that what you think of as an edge-case is covered somehow.

The next thing I will try is using it in a React site (with TailwindUI components)