Apologies for this extremely late review. I haven't gotten much time to spend on Swift Evolution lately.
I think one tenet of good design is the idea that form follows function. This does not mean that the aesthetic of the form doesn't matter. It still does. It's still very important, but the function must take priority over it.
In the case of regex literals, I think their primary function is indicating (clearly) to both the compiler and the code reader that a piece of data should be treated as a regex pattern. Therefore, a good syntax for these literals should be, foremost, fully capable at performing this function.
My impression after reading this and the prior revision of the proposal is that the bare-slash syntax is designed from the opposite direction: a desired aesthetic is chosen first, and then workarounds are found to try to fit it over the necessary function. Even though there are many entries in the "alternatives considered" detailing why the bare-slash syntax is preferred, the rationales provided mostly focus on its aesthetic advantages, with not much on the functional ones. In fact, the rationales suggest some of the alternatives do fit better with their intended function.
I think this design process (if true) has led to the complex parsing rules and ambiguities as shown in the proposal. In my opinion, complexity and ambiguity aren't inherently bad by themselves. Sometimes, they're good, because computers and humans digest code differently, and the complexity and ambiguity in compiler (e.g. contextual keywords) are there to help keep code stay intuitive to humans. However, in this case, some of the complexity and ambiguity is added into human comprehension. This is bad in my opinion, and I would go so far to say that it's actively harmful.
Consider this simple example from the proposal:
baz(/, /)
Under this proposal, this will become a function call taking a regex literal. However, to many people who aren't staying up to date with all the shiny new things we add into the language (as we shouldn't expect them to be), this change is completely imperceptible until they compile/run it and are confused to find that it's not doing what they have learnt to expect. This is a departure from the philosophy of progressive disclosure of complexity that Swift prides itself in: now in order to use unapplied operators properly, a user must also learn regex literals (which more likely than not they'll never need to use directly) to understand how to handle edge cases, and vice versa.
Although tooling (mostly syntax highlighting, I suppose) can help alleviate the problem to some extent, it's external to the language itself and so shouldn't be relied upon as the solution to a problem created by the language itself. There are also speculations upthread to the instability of syntax highlighting given the parsing rules' complexity (and potential additional complexity). We should also remember not everyone has access to good syntax highlighting. Not everyone is privileged enough to be able to afford a Mac and use Xcode.
Even for those who are fully aware of and understand the new parsing rules will perhaps find Swift code become less predictable and reliable. Humans are bad at keeping track of all the tiny details. This is why typos happen in code, why they persist even after multiple careful proofreads, and why sometimes they persist even after the compiler points out precisely where the error is. I suspect details as small as whitespace placement are easily automatically neglected by human brains, and unless the compiler can point out precisely what's wrong and how to fix it, the user will find themselves tripped up and left directionless. All the gotchas combined with the already lengthy compilation time of Swift might lead to more frustration and poorer user experience, and push it further away from being a suitable first language.
I agree with the core team that we should try to make regex literals elegant, but realistically, how elegant can we make regex through the delimiters alone, if we're keeping almost all inelegant aspects of regex? And how much more inelegant can regex be, if the delimiters are inelegant? Is elegance primarily associated with visual simplicity, or is there more to it such as the ease of use and clear reflection of its function? Also, is elegance what many of those who reach for regex care about, and is it worth it to complicate human understanding of Swift code in general for what might amount to rare uses in code?
If the goal is to make regex easier to use in Swift, the bare-slash syntax does quite the contrary in my opinion, along with it makes some other parts of the language harder to use and reason. At the end of the day humans write (and read while writing) code. The compiler can't read peoples' mind, but only reads what's written and translates it for computers. So it's important that we try to make sure what humans think they're telling the compiler matches what the compiler thinks the humans are telling them.