Is it permissible to openly announce the engagement of a woman who is in her waiting period (iddah)?

It is not permissible to openly announce the engagement of a woman in her waiting period (Iddah), but it is permissible to hint (imply) at it if she is in her waiting period after the death of her husband. And Allah Knows Best.

What is the ruling when the duration of the monthly period varies, and sporadically increases?

If the period didn`t exceed (15) days from the first seeing of blood discharges until its end including the times of temporary cessation, then it is menses. But, if the period exceeded (15) days, then the woman experiencing this is Mostahadah (bleeding outside the time of monthly period), and should abide by her regular period, and consult one of the scholars.

Is wearing a cap permissible for boys, or girls?

All Perfect Praise is due to Allah, The Lord of The Worlds.

In principle, anything is permissible sol long as there is no Sharia evidence prohibiting it, thus wearing the cap by boys is permissible as long as it isn`t done in imitation of the disbelievers. Moreover, a Muslim woman should avoid all that which attracts the attention of men because whatever leads to the forbidden is forbidden. And Allah Knows Best.

Is it permissible for a wife to give her money to her family as a charity, or a gift without asking her husband, or seeking his consent?

The wife has the right to give her money as a charity, or a gift to her family, or to other people after consulting her husband out of respect, and this is the meaning of treating on footing of kindness and equity. Therefore, if he wanted to stop her from helping her family, then there is no harm in not telling him.