I've been curious what a "Tailwind Linter" plugin for Figma would look like....
And when you watch Adam's screencasts, you'll see him take a design which has some "custom" pixel values and then use his judgement to snap it to a built in size.
The modern web and pixel perfect design is a combo that doesn't mix and any good designer would know that.
Additionally, this is a good example of the tooling overstepping bounds. Developers giving feedback that their tooling can't match designs made to fit existing brand standards is naive and doesn't reflect business reality.
As a counterpoint though, I definitely see merit in Tailwind for new web-first applications where the development team can align with designers from the outset.
Many designers I have known think of consistency in terms of branding (at most). There is almost always some weird edge case that means a new font size, or unique spacing. Get enough of those, and the design system falls apart.
Some are better than others at this, obviously, but the mix has not really been in consistency's favor (though I will admit it has been improving the past few years).
While I don't disagree with your points, there is still ground to be made here.
1) If designers had a "tailwind linter" in their design tool from the start, I believe that they would be encouraged to use it from the start and would start tweaking their designs from the get go to look just as good with it.
The same principle applies to code linters. There are exceptions where developers can disable a linter for specific pieces of code, but having it there encourages the code to be "constrained" in a consistent way.
2) Just because a design has a "13px" padding doesn't imply the designer thought "13 pixels is the best value here and 12 pixels is simply unacceptable". A design linter would help with the "expressiveness" of the design and when things truly are "exceptional" cases.
Note 2: I'm obviously recommending a technical solution to the problem very early in the design process, but the way I solve it now is by discussing it with the designer over a zoom call. I'll show them the design and say "does this look good? I deviated a bit, is that ok?" It almost always is, which is a win for everyone.
Basically, we're asking workaday designers to design using a tool that doesn't respect the implementation constraints, and doesn't allow them to preview at arbitrary window sizes.
Good designers will also want as few values as possible. They are creating visual system. I doub't they will want to have 20 different font sizes and padding left values. If there is fontsize 26 and 29 its most probably a mistake because nobody can differentiate the size so it has no function.
It really needs to be 28px this time for some sorta-legit reason? Fine, add a semantic class (or id) for it that's not part of your tailwind framework, kind of dropping down to "usual" CSS
After a while, you get the amazing benefit of simply being able to copy and paste HTML from one place to another - since the class names are common, you can copy HTML directly from a design mockup into your application, with only minimal extra work in templating. This is much more efficient than trying to figure out pixel-sizes in a PSD, then trying to figure out which combination of CSS classes will succeed in reproducing the visual appearance (most of the time, in most browsers...)
Take the time to communicate with the designer to define color shades/palettes, margins, typography and so on. This can also lead to discovering relations and components and intent.
The only serious issue I had was when implementing designs provided by an outside designer:
1. The design says this width needs to be 28 px
2. That'd be "w-7", which TW doesn't provide. Guess I'll add it to my tailwind config file.
3. Repeat ad nauseam until I broke down and added all "w-n" widths to my tailwind config from 1 to 500.
4. Repeat for min-width, spacing, border-radius, etc.
The result is that A) I get really good at converting pixels to rems to tailwind-scale, then back again in my head and B) My tailwind config is huge - the saving grace being the purge tool that gets rid of unused styles.