In that small/medium sized company space there are those that publicize nothing about themselves and have such a poorly written JD that tells you nothing about why they exist, their goals, or anything more than possibly irrelevant keywords, then have the requirement for a cover letter. In this instance, they haven't provided a shred of evidence for why someone would want to work with them. I normally see this when non-technical people attempt to hire technical people, they just lack understanding for what is important and are sometimes fresh to hiring in general; less so when technical try to hire technical (but still appears).

I'd rather have a conversation with someone who isn't HR, cover letters are mostly wasted effort.

If you don't have an appropriate contact, sending a good cover letter and acceptable resume to someone who isn't HR is the first step in getting that conversation in my experience.