Can Money Buy Happiness

I think that the old expression "money can't buy happiness" is a true one. This is true in the way we select our work or change from one job to another. Since I will soon stop working and become either a "retired gentleman" or a "lazy bum" (you decide my title) thoughts about this subject come into my small brain.
I have enjoyed being a teacher, made enough money from that and had great investments and an inheritance that make me well off to never have to work again. The one temptation that never beckoned me (but that mst people succumb to) was the desire to quit my job in favor of a higher salary and more benefits. That "I am taking this job even though I will hate the work" mentality is a way of thinking that just about everyone considers at some point, no matter what the person's current salary is.
It's because we are all trained by society to believe that bigger is better when it comes to our paycheck. This explains the "climbing the corporate ladder" mentality. Many people job hop strictly for the money. Nothing is wrong with it for some. Surely striving for a better material life is a noble attempt and improves society.
But society tells us that we should all go for the money, making job satisfaction a secondary factor in our work career. For me the money was secondary. One's love of his work far overshadows the extra money a job might bring if the new job would make us hate going to work.
So when is "enough enough"? Why put your whole life into potential disarray just for more money? You risk misery when taking that promotion or new job just for the money it offers. At what point does happiness in what you do-or at least job comfort exceed an extra zero on your paycheck?
Ha! I am done with work and have no regrets I chose the job satisfaction option. What makes it so complicated is that many other people who choose the money trail are just as happy with their choice?