From personal experience I can say that my sister's auDNA has matches to people who I do not. Moreover, she has some of my father's X-chromosome, where I do not. So in the case of a brother and sister, I can say there are distinct advantages to testing both. Even with siblings of the same sex, they may inherit different sections of auDNA and match different people.
Ditto for my first and second cousins. We share many matches, but some much more than others. Triangulating on our matches allows us to indentify ancestral origins for specific sections of our DNA. I would always recommend testing older generations if they are available and willing. I would not test a male cousin if my uncle is available.
X-Chromosome matches and mtDNA data can also be important for cousins. The way these elements are inherited should be considered when evaluating subjects for testing. If my father is dead, but my mother is alive, I would test both my mother and sister for X-chromosome purposes. (The same cannot be said for testing father and son.)
I tested my daughter mainly for the purpose of Health Markers, not genealogy. However, from a standpoint of curiosity, we have enjoyed examining our chromosome matches on Gedmatch.com where we phased our results. We can see exactly which portions of her auDNA (more than half) inherited from me.
auDNA is not as predictable as many people imagine. I have learned to make no assumptions about who I or other family members might match. For those with more a passing interest in DNA matching, more testing can be helpful, or at least it has been for me.