Occasionally when I am trying to figure things out with someone asking a question, I come to the conclusion that it would be better to use the chat. This typically happens well before the stage where the software will automatically prompt ("Comments are not for extended discussion. Would you like to take this discussion to chat?"), and sometimes even a third party will intervene ("could you please take this to chat") before the software would come to that conclusion.
The problem is, it is an incredible amount of work to actually do so, and even I - as a nearly 10-year veteran - struggled to figure out a way to do it at all.
See, I did the things that are expected of a self-reliant problem solver. After failing to observe anything in the UI directly, I did a web search and managed to find a 9-year-old (!) meta.SE post with comments (!) claiming that there is a
"Chat" link at the top of SO and every SE site. That still didn't highlight the next step for me, but it at least offered a hint. Eventually I figured out that that there is a plain text, normal-sized, linked word "chat" (!) between "help" and "log out" (!!) inside the drop-down menu on the far right (!!!).
I want to make it clear here that people can use the Stack Exchange network perfectly well day-in, day-out without ever opening that menu, or even necessarily recognizing it as a menu. So it seems miraculous to me that I was even able to figure out that much, and have no idea how or why I should be expected to know about this obscure "chat" link.
But even then, it does not solve the problem. Once I have clicked
chat here, I - apparently - have to scroll to the bottom of page 1 of the list of existing chat rooms, find and click a "create a new room" button that is labelled in quite small text, fill out a form to create the room - and then go back to the original post in order to write a comment manually including an invite link.
All of this to reproduce what is single-click functionality - but only when the system arbitrarily decides that it's had enough comment spam.
I am on my hands and knees - please help me to avoid spamming comment sections, because I do not want to spam comment sections. It has been nearly 9 years that people have been asking for this, and now when I search I am sent around in circles of such ancient meta posts (1, 2). As far as I can tell from those posts, there has never been a non-trivial objection to this feature, just... a lack of action. The last link in particular shows many well-respected community members filing in at various points over the last 9 years to voice support.
I don't understand why the site bothers to offer chat functionality at all if it's going to be this obscure. I have an easier time figuring out Wikipedia governance's internal processes than this.