Money is a funny thing because it is super important, yet at the same time, not all that important. Or rather, not that it's not important, but that it's not a very good purpose in life. It's great as a tool. It absolutely buys short-term happiness. But you can be miserable with lots of money too. The collective wisdom of the reddit threads I've seen discussing this topic is "being rich doesn't buy happiness, but it makes being unhappy a lot more comfortable", so you'll have to find your long-term happiness & your permanent happiness elsewhere. The pursuit of money can sometimes cloud judgement, too. Freakanomics had a good piece on drug dealing; the TL;DR is that the foot soldiers averaged $3.30 an hour & the officers made $7 an hour, and many crack dealers still lived with their moms:
http://articles.latimes.com/2005/apr/24/opinion/oe-dubner24
I think of money as a representation of your time & effort from working, and if you've inherited wealth, then think of it as a gift that you shouldn't squander. I think it's important to live a lifestyle within your means & to manage it appropriately for your situation. I know plenty of people who do really well financially but don't go crazy on buying stuff, so they don't really have to even bother budgeting, but I also know plenty of people making $100k+ a year who are literally living paycheck to paycheck. At least in the United States, we have all kinds of predatory practices & traps out there to be aware of...credit cards with 26.99% APR, student loans with ridiculous payback terms, long-term financing that can double the original purchase price over time, etc., which can really cause a lot of stress. Finances are still one of the leading causes of divorce, last I read.
But no, I don't think money buys real happiness. Money can buy a lot of freedom, financially-speaking, but I think happiness really has more to do with other factors, even simple ones like attitude. There are plenty of people out there who are determined to be unhappy, and no amount of money will change that. I do think Mr. Simmons has some good points, with Maslow's hierarchy reducing financial stress as you go up the ladder, access to better healthcare, etc., but I don't think that money buys real, lasting happiness. For perspective, one thing to keep in mind is that he is offering advice as a guy who has made $300 million cosplaying while singing & being on TV since the 70's; I'd imagine it's hard not to live in an Ivory Tower-esqe bubble after being that wealthy for 40+ years & having a nearly billion-dollar merchandising brand.