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Hmm you said you paid cash for all your cars but sometimes it's smarter to finance or lease. Being able to pay cash outright is great but not everyone can do it.
And aren't you being a bit presumptuous by assuming he doesn't work hard? If he's working a good job while in school and can afford to set aside some money for monthly payments towards a car then why not? Isn't that why we work in the first place? To be able to get what we want? You also mention being able to enjoy life... Well driving an s2k is a great way to enjoy life.
Of course OP should be smart about where he spends his money. If getting the s2k will stretch you too much then it's better to wait. If you can comfortably afford it then go ahead.
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