That makes sense to a point, but the first time you miss a client meeting because your beater broke down on the way, the value of having something a little newer/better becomes clear.
Yes, I learned the hard way. Once. Like you, the "newest" car I ever owned prior to buying my M.B. was a 1988 GMC pickup. And I got it in a trade for my '86 Dodge Daytona - in 1995, so it wasn't exactly "new" then either (and I kept it for almost 10 years).
Shoot, the M.B. I'm driving today cost me less than a new Honda Civic costs with only 50k miles on it, so I guess I did okay. It's never left me stranded and is a great DD. Point is, there's reasons for things and even though some things might not make sense at first glance or on the surface, they might possibly be well thought-through and/or have good and legitimate reasons for them. . .