1. I did not overestimate, it still took you days. spreadsheet would be done monday night. sidenote: C# backend CRUD might be a very different market than what OP is looking at
2. this is true, but with kids there is also extra risk in changing jobs. not enough to say dont do it - but it's a consideration.
3. he is a web developer turned tech director, not a software developer. without formal education in the field. We do not know his situation, and this type of thinking is what gets people into the most trouble. that 12 years of experience might not be fully industry relevant.
Overall I do agree with you, it sounds like it is definitely worth the effort for him to find a new job. But it is a common trap to shulk responsibility for your current situation by thinking things will be different after some specific life event. that said, he posted info baout his situation after my initial post and yeah he should find a better job if he can but i dont even think hes in trouble.
TBH I think OP was either just venting or baiting for someone here to hook him up with a web-dev side gig.
Also, He is isnt even living paycheck to paycheck.. hes paying off a mortgage so he's investing in real estate around NYC, which has increased a lot over the past year alone so odds are this guy is far from debt.