For the first of your two questions—what was life like for 14th c. women?—there is an excellent, general-reader friendly book on this subject by Judith Bennett: A Medieval Life: Cecilia Penifader of Brigstock, c. 1295-1344.

As for "rising through the ranks," it was quite common for peasant women to take leading roles in managing the financial health of their families or in their community—Judith Bennett, for example, has written about how women would brew ale and sell it for charity or to gain an extra source of income at points of hardship. If you are asking if it was possible for women to change their social station through marriage or other means in the fourteenth century, I would defer to someone better versed in the complexities surrounding the debate on the English Gentry during this period.