Is it worth it to wait a long period for a new job?

Isn’t the question very insensitive? Like why you want to guess if his skill sets are poor? Or approach? Clearly, he has tried hard but failed to get the desired outcome (I am interpreting that from “financial stress” part). Getting a job isn’t always about skills/approach, it has other things (macro situation, luck) as well. Otherwise, people those who were making big in 2022 aren’t out-of-skills suddenly in 2023.

The wait should depend on the stage of your career and your financial condition. In early stage of the career, waiting long doesn't make sense. Go for BA, PA, DA, PMM, you can still pivot later to your career preference. You also get to learn diverse hard skills and work towards different metrics. Also, each month of experience is valuable then (For 3YOE, a 6m wait is loss of a sixth of his experience) This changes as your career progress. At 10YoE, most roles will have more managerial tasks, hard skills don't define success a lot, and hopefully are resilient financially. So a 1Y break would not set you back as much then. However, a break might wear you down with anxiety if your work is major part of your identity, so plan for that. PS: Had been on a 20 month break total in past 3y