In our family going back to my earliest understanding of adult things and any friends close enough to know their private business, the biggest challenge is unpredictable medical issues that max out medical coverage, or have effects beyond medical care, or good old simple mental malfunction, addiction, and relationship drama and rebound. Not just you, the wife and kids, but parents, siblings and others close to you, and eventually grand kids.
Any one issue is pretty rare, but the world is full of money sucking issues and hard choices that increase with age.
Our financial advisor friend was about to retire - has every legal form known to man, has great income updated on a spreadsheet many times a day, beautiful wife, happy adult kids, great cabin in the woods, nice teeth, mostly natural hair, cautious driving discount, probably volunteered to walk puppies and served Thanksgiving dinner at the homeless shelter. Recently got Covid and died.
There’s no real advice in all this - nothing all of us don’t already know.