@Dinsdale, first, no need to bother with the “cap A” button — unfortunately, that won’t actually help you here because the other editing mode still has the same issue
Not your fault; it’s just a software flaw.
I can sympathize. It sucks having these little unexpected gotcha “landmines” all over the place. My own, similar pet peeve for this forum is when you try to end a sentence with a : (colon)… it thinks you’re trying to make a smiley and auto-incorrects it into :slight_smile:, even though I’m just trying to make a new list after the colon. That, and the inability to post images easily.
The thing is… we as SDMB users are kinda caught in a convoluted three-way bind, with no easy way to change anything about the forum:
For one thing, the forum itself (as in its current owner, the Chicago Sun Times), does not make or maintain this forum software. That’s a third-party forum program, Discourse, made by a company who sells it to hundreds of thousands of communities and millions of users. They try to target a middle ground between adding features and maintaining simplicity, but they can’t please everyone. I personally wish they leaned more towards simplicity and ease of use, but we don’t get to make that call. They do have their own forum at https://meta.discourse.org/ if you want to complain about the software itself. Myself and other SDMB posters have brought up a few issues there in the past, to mixed success.
For another thing, Discourse itself is usually highly configurable, but in our specific case, our owner-administrators are not around very much to change small nitty-gritty technical details like this. My understanding is that they are involved in major, high-level decisions (like our move from the previous forum software to Discourse, years and years ago) or major changes to the rules and such. But otherwise they are normally absent. But hey, they also pay the bills and keep this forum alive at no charge to us!
And lastly, there’s always going to be different ideas within the SDMB poster base about how to deal with any situation like this. Should we turn off dollar signs for everyone so users don’t accidentally enter the math mode? Should we leave it on for the convenience for the people who do frequently type math, especially in General Questions? It’s necessarily a compromise with tradeoffs. Maybe there are some more custom solutions (like fixing the WYSIWYG editor so that the dollar signs don’t work there), but again, without the admins present, we can’t do anything of the sort anyway, so it’s a moot point.
So as free users of a beloved forum without any tech admins around, we’re just kinda stuck with its (numerous and annoying!) quirks. This is just one of them 
It sucks, but there it is…
If I were you, I’d just keep the backslash character in mind, like \$. The \ is Discourse’s universal “escape” character that disables the “magic” of the subsequent character, whether that’s a $ or a - (for forming lists) or ** (for bolding). It’s an extra step, yes, but at least it beats never being able to use certain punctuation marks…
But anyway, I feel ya. I think it’s just one of those “pick your battles” moments.