Am I crazy to quit in this market?

I'm currently stuck on what to do with my job..

Some background that factors in to some decision making without getting too sappy. About a year ago my mother passed away from cancer after a very quick 2 month diagnosis and my dad passed away when I was a kid from cancer as well.

After my mom passed, I quit my job (software), took a couple weeks to go to Europe, then came back into a completely different position that I had lined up in a completely different field (house renovations). I'm handy and used to do this type of work when I was younger so thought maybe the switch would be beneficial. The company I was working for had a fire incident on a massive home, so they no longer had work for me and had to let me go.

I got hired back to a sister company from my last one, and was hired on for a position that I did not want to do, as I've done this role previously and despised it (PM).

I am now severely struggling again in this position due to lack of leadership, support and onboarding about a year in. I'm on a massive project that I can't succeed in + 15 small projects and am severely stressed daily.

I'm in a solid position financially due to the unfortunate circumstances of losing my parents (No mortgage on my home + rental properties + $170k in investments). The rental properties generate around $1700 a month and cover my base occurring monthly expenses (groceries, gas, insurance, phone etc).

I've never quit a job without any plan, or anything lined up etc in 8+ years and always try to think 3-5 years on any major decision I do. I'm so stressed from my job, and things aren't getting better as the company is loading on more work even though I've told them I don't have anymore bandwidth due to all the projects I'm on. I know the job market is terrible as well, and I've been applying to jobs like crazy the last 2 months but have heard nothing.

Is it crazy to just take that leap with nothing lined up?