What did a medieval lady-in-waiting earn?
40 pounds a year in the queen's service.
About $6,500 a month in today's gold.
A month of that pay weighs about as much as a hen's egg in gold.
Forty pounds a year for being the queen's sister, professionally.

Where the money came from
Anne Woodville was born at Grafton Regis in Northamptonshire, one of the fourteen children of Richard Woodville, Earl Rivers, and Jacquetta of Luxembourg. Her elder sister Elizabeth married Edward IV in secret and was crowned queen. In 1466, a year after the coronation, Anne became one of the queen's ladies-in-waiting, paid £40 a year for her service. It was a small, close circle: in the middle of the century the queen had only five ladies-in-waiting. That same year the king granted his queen the palace at Greenwich. The post opened the door to a grand marriage. The queen matched her brothers and sisters with heirs of the greatest families in the realm, to add to her family's power and wealth. Before 15 August 1467 Anne married William Bourchier, son and heir of the earl of Essex, himself a great-grandson of Edward III. The couple were given lands worth £100 a year, two and a half times her wage. The matches angered the old nobility, and in 1469 the earl of Warwick had Anne's father and her brother John put to death. Her £40 was still a fine wage: by one estimate for these years, an archer might expect £9 a year and a knight about £60, so she earned more than four times an archer's pay, though only two thirds of a knight's.
Sources: en.wikipedia.org · en.wikipedia.org 2 · en.wikipedia.org 3 · en.wikipedia.org 4 · kinghenryvi.com
What a lady-in-waiting's pay bought in 1350
a pound of pepper: less than a day's pay
a cow: 6 days' pay
a year's food for one adult: 4 weeks' pay
a great stained-glass window: 2 years' pay, more than a whole year of it
a warhorse: 3 years' pay, more than a whole year of it
Every price of 1350, with its source, is on the prices page.