This speaks to OPs mention of "brokenness on both sides" where being able to write a cover letter and tailoring the resume to the job is considered "privileged"

Please note, I'm not disputing your comment at all. It's just that what used to be considered the norm (cover letter, etc) is just way too time-intensive by the wayside as applicants now have to mostly optimize for quantity of apps submitted.

If you don't NEED a new job ASAP then, yeah, you can do that, but for someone who's been laid off or unemployed for longer stretches, it's really just a numbers game most of the time.