Strategy for submission of articles to highly ranked journals
I am not an editor so I don't think I can definitely say how editors treat this, but I suspect that if you keep sending manuscripts that are not appropriate to the journal, it won't be helpful in promoting your next submission and won't gain you respect. Consider the fact that you have to convince the editor why your manuscript is important in the cover letter - you don't want to keep sending a paper every week saying it is the most important paper of the decade. Even as a reviewer I can tell you it is annoying to review a paper that is clearly not suited for the journal (although maybe it is the editor's fault that it passed to review in the first place).

If you think your manuscript fits a high-impact journal, it is fine to try a few journals to increase your chances. But try to be sincere with yourself - many papers belong to specialized journals, and that is fine.

Another fact you might want to consider is that high-impact journals tend to get recognized experts in the field as reviewers. You probably don't want to gain a bad reputation in those circles. Second, the pool of experts can be pretty small which could mean that when you resubmit to a different high-impact journal, you will get the same reviewer or someone who already heard about the paper and is biased (yes, sometimes reviewers mention papers they review to colleagues).

So the bottom line is: it is ok to resubmit a few times, but be careful not to overdo it.