You bring up lots of good points here.
I also see that having a job gives a little "security" in terms of if something happens unexpectedly, or with the economy for example. Having two jobs increases the protection. As long as not expanding lifestyle to swallow any increases in income, when bad things happen, there is a cushion. I have found this reassuring mentally for me, especially considering how hard the first years were with Smallsteps.
Commitment, time and money... without it everything is damned more difficult.
Yes. Money can't buy happiness, but it can insulate against the conditions that lead to struggle, pain and suffering. At least in regard to some things.