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Mostly, I've heard that having previous publication credits to your name is beneficial, but I wonder if listing many publications in journals that aren't particularly well-known or impressive might make a worse impression than just including a small number of publications.
I'd appreciate answers from journal editors or from people who have been published in multiple tiers of literary journal and therefore can speak from personal experience.
How less well regarded are they?
Unless your previous publication experience consists of "Dear Penthouse: I never thought this could happen to me..." then I would leave the bulk of your experience in place.
That being said, if you have extensive publication experience I would prioritize the more prominent publications first, keeping it to about 5. The time you got published in "Regional Writers Quarterly" should probably take precedence over that time you wrote an article for "The Weekly Freebie".
And that being said, I have always, ALWAYS, found that the cover letter is far, FAR less important than the what comes after. An impressive cover letter might get you a more eager reader (or just plain read) but if what comes after doesn't impress, your cover letter is essentially meaningless.
As someone that's submitted papers to scientific journals I can say that the feedback I received was no, in the case of a scientific paper, it isn't detrimental. It also doesn't help at all, as science papers are judged on their merits alone, ostensibly, but I've always gotten the impression that the editors are more likely to take an entry from someone with published work seriously. I'm not certain if this is helpful to you or not, but, I'm posting it in case it is.
