Interesting thread. I literally just went through this as I bought my first pin last week. I'm early 30's certainly not rich but I do ok. $5000 was a fair sized investment for me, especially for someone who primarily collects video games. $5000 on a single game was tougher to justify. I like Modding it, doing small easy upgrades that personalize it, and just learning to start tinkering. I can definitely agree with a lot of what people have said on here that buying NIB is not the best idea. I bought a BDK that was in great shape. A good fully working HUO is a good purchase for a new pinball owner and no matter what game you have to be interested in playing pinball almost daily you will need a little variety which is why so many people say once you buy one that there are more sure to follow.
You are used to being 100% player and not worrying about fixing. Fixing is half of the hobby of owning a pin AT LEAST. If you just like playing and no interest in fixing a NIB won't save you. You will have to fix it and probably sooner than you were hoping. over the past 2 weeks I have made a couple small fixes to my game and have one larger fix I will need to figure out but have some help from people on this forum. That's from a game that was 100% working when I got it.
As far as "happiness" goes. personally I find games give me a more shallow happiness. I'm very happy when I am playing the game or I get a high score. But soon after sometimes even 30 minutes after that happiness fades. But Spending time with children, nieces/nephews. Going to the lake with friends and family. spending time walking with your spouse on a beautiful evening, or going on a vacation. These things have a lasting happiness that gives a person memories and fond feelings. I do think there can be a deeper sense of "accomplishment" if you are fixing a machine or bringing an older machine back to life but accomplishment is only a single part of overall happiness. But happiness has different meanings for different people. For me I think the way to achieve happiness is balance. everything balanced in life between games, family, friends, vacation, hard work, even rest. I don't think buying materials brings lasting happiness and sometimes people with the means will continue to buy new things be it pinball machines or video games constantly to chase that initial happiness. Once the shallow happiness fades a new thing needs to be purchased to keep feeling happy. I have been collecting video games for 20 years and now have a few arcades and a pinball machine. I enjoy them in my spare time and sharing with friends and family but at the end of the day my true happiness comes from my experience and bringing happiness into other peoples lives.