Yes, the small caps you're using are bad for machines. People also may have issues with them.
AceCalhoon pointed us in comments to a question on Super User about the usage and purpose of these glyphs. The top answer explains they're not intended for usage as regular written text, and that trying to use them that way breaks stuff:
Those characters are not intended for regular Latin-alphabet text but for phonetics, Cyrillic-alphabet text, for use as mathematical symbols (representing variables), or similar.
I recommend just bolding or italicising your special terminology (e.g. as Let us discuss this further or Let us discuss this further), and picking a more ordinary sort of title. I would recommend this even if machines could handle the small caps.
This analysis strictly applies to using the Unicode smallcaps characters to assemble smallcaps text, and does not reflect upon small caps in general. PDFs have a way to make small caps machine-friendly via providing a machine-friendly layer. Websites can also make screen reader friendly smallcaps via CSS styling, but that isn't available to us via markdown.
Screen readers: unintelligible
I downloaded the latest version of NVDA, one of the popular screen readers I'm accustomed to from my accessibility work, and ran it through your question. What it read out was mostly unintelligible. The small caps sections were gibberish, and it was hard to recognise when the normal English words were starting again before the screen reader had already dived right back into another section of gibberish.
Out of concern your generator may be using Cyrillic characters where it should instead be using the Unicode standard small caps, I assembled the text "ʜᴇʟʟᴏ ᴛʜᴇʀᴇ" using excusively those Unicode small caps. It was similarly unintelligible.
The Unicode wikipedia article I just linked has certain paragraph text in small caps. It's perfectly legible. It's rendered in small caps due to the CSS styling I mentioned above, however.
Google: can't work with your smallcaps text very well
If I google for the text "struggling with escalating" on our site, I find your question just fine. Google has your question indexed. You'll notice the "struggling with escalating" phrase is bolded in the search extracts.
If I turn it into "struggling with escalating" but only if or "struggling with escalating" let us discuss this further, none of the small caps text is bolded.
If I search specifically for your smallcaps text with "struggling with escalating" Lᴇᴛ ᴜs ᴅɪsᴄᴜss ᴛʜɪs ꜰᴜʀᴛʜᴇʀ, Google bolds that text just fine, indicating it doesn't treat the Unicode smallcaps characters as equivalent to ordinary text.
Google Translate has no idea what to do with the text "Lᴇᴛ ᴜs ᴅɪsᴄᴜss ᴛʜɪs ꜰᴜʀᴛʜᴇʀ" but can work with "Let us discuss this further" just fine.
People: may dislike it
Small caps usage can be a useful formatting convention sometimes. When established as a standard style in a document it can be very useful for helping special terminology stand out.
RPG.SE doesn't use that convention. Instead, our formatting choices include bold and italic for special terminology, and we can use those regardless of how they're formatted in the RPG's text.
Bucking our common formatting conventions can be unwelcome. In this case, the esoteric title and body text can be seen as an attempt to grab attention, and Stack Exchange users generally dislike attempts to grab attention whether via esoteric titles, funny images, or other methods.
The book using small caps as a convention is fine, but that's a convention that requires translating into a different equivalent convention here: bold/italics.