Bottom line: The ship was late and met with a headwind.
The first part of the League, "People are poor, but it rains all the time", said that people are already poor, lack food and clothing, and their houses are in tatters, but the house leaks all the time.
In the second part, "The ship was late and met with a headwind", the fleet set sail. My ship was already late, but I had no sooner set sail than I met a headwind and had to go against it. How can we catch up with the fleet?
The upper and lower couplets are used to describe things that are not going well, which is even more difficult.