Struggling with InDesign and Adobe Acrobat Pro. Possible User Error?

EDIT: Thank you so, so much for the advice already everyone. It's rapidly becoming clear it's primarily user error on my part, although I'm still mystified by the span tags in my list item labels. Hello all! I'm asking for advice as I can't tell if the issues I'm having with Adobe products are user error or not. I've asked in the InDesign reddit as well, but haven't gotten a clear solution yet. I'm really hoping it's user error so someone could let me know what I can do to fix it, and the reason

• Struggling with InDesign and Adobe Acrobat Pro. Possible User Error?
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