Actually, Wan Youde has a skill, so finding work at a wealthy household wouldn't be a problem. However, his son is a fool, and he has an elderly mother. Wealthy households don't want someone bringing in so many burdens. On the other hand, Wan Youde doesn't feel reassured leaving his wife alone to care for both the elderly and the child. As a result, he's been muddling through life like this.
He came to the academy for a job because they said anyone with a skill could apply. He applied just to try his luck, never expecting that he would actually be hired. Not only does he receive a monthly stipend of one or two pieces of silver, but he also gets a separate courtyard to live in and food for his entire family. To the point that after they moved into the courtyard behind Xuan Hall, they still felt like they were dreaming.