the major stumbling block has been how tailwind is mostly just css translated into its own hard-to-memorize lingo.
For example, say I want to do something basic like "display:flex; justify-content: start".
In tailwind you would type "flex justify-start" instead.
Which doesn't really follow any rules as far as how to get from A to B, so it's just a matter of having to look the magic word up in their docs each time until you memorize. And there are a lot of keywords (many modifiable according to n-dimensional properties) to memorize.
I know there are handy slugs like "w-1/3" that encapsulate a best practice - but I'm a person who'd rather master the underlying mechanics of that best practice and be able to deploy, tweak and debug it myself.