Is it permissible for a person who has to make up for missed fasts to fast six days of Shawwal (the month directly after Ramadan) before making up for the missed fasts?
Yes, it is permissible for him/her to do so, but it is better that they make up for missed fasts first. And Allah Knows Best.
What should a woman who delayed making up for missed fast, due to menstruation, till the start of the next Ramadan?
Whosoever broke fasting in Ramadan, and was able to make up for it, but didn`t until the next Ramadan started, is obliged to make up for the missed days, and to pay the ransom as well. However, if he/she wasn`t able to before next Ramadhaan due to an excuse, then he/she should only make up for the missed days. And Allah Knows Best.
Should a pregnant woman who broke fast because of pregnancy make it up, and is a ransom due on her?
The pregnant and the suckling, if they fear for their health, may break their fast and make up for it, and no ransom is due on them. However, if they broke fast in fear for the fetus and the baby, then they are obliged to make up for it, and pay the ransom which is feeding a needy person for each of the missed fasting days. And Allah Knows Best.
Is it incumbent on a family to provide for its old handicapped son and take care of him?
The family and relatives - e.g. brothers - of such a person are obliged to spend on him and take care of him if he didn`t have money of his own.