Sounds like you are already compromising with the 991 as what you really want is a 997. My personal view on Porsche has always been that they make amazing overpriced cars. I know multiple people that bought a “cheap” used Porsche only to regret that decision within a year due to insane maintenance and repair costs.
Same as you I grew up in a paycheck to paycheck household and while I do OK now I still always look at the value my money is buying. I’m not at a point where money is no object. On the other hand I’m nearing half a century on this planet and realize I won’t live forever. So enjoying things now while I still can while not being financially reckless is definitely a thing.
To that end I bought a used V8 F-Type convertible and enjoying the heck out of it. I care about all my cars and I get equally upset when I find a door ding on my wife’s Honda CRV as I would on my FType. If I had disposable income to afford a car I wanted and it would bring happiness to my life in this miserable year I’d go for it. Life is short. Enjoy every day like it’s your last.
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