I'm really sorry to hear about your friend's tough situation. It's understandable that he's hesitant to take a job without proper benefits and stability, especially with his wife's health concerns. It's great that you're supporting him in his job search. One piece of advice I have is to explore alternative options like freelancing or remote work, which might offer more flexibility and potential for higher pay. Encourage him to network, update his resume, and consider any transferable skills he may have. Remind him to stay positive and persistent.