Bromination of ethyl substituted benzaldehydes
Your first query is genuine and the 2nd product for the first case is wrong. It should be, as you noted as well, 5-bromo-2-ethyl-benzaldehyde.

Regarding your second query, you're wrong. Recall the general rule that:


when more than one activators are present on the same benzene ring, the substitution is governed by the best activator alone
when an activator and a deactivator is present on the same benzene ring, the substitution is governed by the activator alone
when more than one deactivators are present on the same benzene ring, the substitution is governed by the weakest deactivator alone


So, here $\ce{Br}$ will go to the o/p position of ethyl group. 



Note that in the high school context, I've assumed we're only talking about the major product, because otherwise, all types of crazy products are generally formed, but in smaller ratios