I am aware of the ethics around submitting papers to multiple journals simultaneously. I know some people have also asked about submitting simultaneous papers to the same journal. In that case, there is hope that maybe they'll all get accepted. I am instead concerned with sending multiple papers to the same journal sequentially (i.e. a month or two apart) when none of them have been accepted.
I am in a situation where I have a large database that I use for analysis (healthcare related field). My collaborators often want to shoot for the same top journal in our field. I have been rejected multiple times already from this journal (all desk rejections), and worry that I could generate a negative reputation with the editors ("Oh, another article from _____, reject it.") even if some of our later studies/findings are more impressive (though to be clear, the prior studies have all been rigorous, asked distinct questions, and were not "salami" science). My collaborators are largely different for each project though so I don't believe they share this worry.
Is this fear warranted? Do editors even remember individual submissions? (my dataset is somewhat unique so I have at times thought they would remember me because of it).
Edit: I spoke with an associate editor of a journal who suggested there was not much to fear in repeated rejections and that we should aim high, and that most decisions from the top journals are desk rejections. It seems opinions vary on this.