Tailwind-UI looks very interesting and I would have no problem paying for it, rather than getting a "free" version, if only for the long-term sustainability. Community projects often go through endless rewrites, and suffer from feature creep and lack of direction.
In a business setting (I run a self-funded SaaS business) I am much more interested in a framework that fixes bugs and is stable.
The only thing that worries me is that the pricing is one-time rather than subscription. How can the authors expect long-term sustainability with a one-time payment? Maintaining a CSS library is a continuous effort, not a one-time thing.
I think if utility-css frameworks get popular someone will abstract the components from the frameworks and things like tailwind ui will become unnecessary (rather it will just be utility-css-ui and will work with any css-framework that implements the "interface").
Semantic UI is the perfect example of why you shouldn't go with something that's generic. Unfortunately the project just became too bloated for one person to handle. Your concern about sustainability is a good one and that's exactly why many of the frameworks' authors sell themes. However, themes usually require a lot of work and are difficult to implement using the actual css framework. tailwind ui is different because if you had the theme it's really easy to recreate it because it's utility first.
It is described in the Tailwind docs here - https://tailwindcss.com/docs/utility-first/
There are tons that look visually appealing, but very few I've found that take a component-based approach (where they document each component individually - or think about how they interplay with each other). I've found the CSS is usually muddled, they often have legacy build pipelines that has to be rewritten to fit with Webpack, and a distinct lack of flexibility.
If Adam solves that side, Tailwind UI will be worth the money.
If it causes other theme providers to up their game, even better.
a) how hard it is to make a library like this that's any good
b) people will want to support them anyway
$249 (or $599 for a team license) one time is really very little if it does what it promises.
This is quite doable for us at Protoship (we've built both a design-to-Tailwind CSS+HTML converter as well as a webpage-to-Sketch Chrome extension). It is a very appealing idea - to be able to recast any webpage into a Utility CSS framework, but I'm curious to hear about situations where it would've been useful in commercial work.
Tachyons is licenced under MIT too.
When your job is delivering high quality UX and there are always more apps to build in the pipeline, having someone give you a library of useful components works.
I have licenses for probably 4-5 of these, and they've all saved many hours of time, and resulted in avoiding the cost of a dedicated designer.
No because I believe that for every enterprising person wanting to circumvent paying for software, there are that many people who want to support the entrepreneurial spirit Adam and company show, and pay for good work. That's what capitalism is suppose to be about at least, anyways.
Normally with themes it would be time prohibitive to do so, but the nature of utility-css is that it's relatively straightforward to implement each component, even without looking at the CSS that's obviously easy to inspect.
I think what they should do is build a tool that let's you build your entire site using these components and charge for that. Otherwise, I guarantee within a year of today, 2/26/20 there will be a free version of this on GitHub created by the community.
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On a side note, if some bored person out there wants to make a huge splash in the CSS community, figuring out a way to target a specific DOM element, create the equivalent of an AST and specify a "dictionary", which would be a utility-css framework (tailwind, tachyons, basecss, etc) and finally reimplement the targeted DOM element in the chosen framework would be amazing.
Assuming you buy into utility-css, that would remove all existing friction in adopting it. Then that would mean you could grab an existing theme [1] and convert it to tailwind components as desired.
1 - https://themes.getbootstrap.com/preview/?theme_id=4231