Bottom line is, a car is transportation. If it isn't transporting, or if it is transporting but only while you grit your teeth til you get home, or if it isn't very enjoyable transport anymore, why bother?
Case in point - 93 400E, awesome car, but clearly not ANYWHERE near where my 97 C230 Starmark car was when I sold it at 170k (the 400 has 182). The old C, in retrospect, was the best Benz I ever owned - and it was tight and made me smile to drive. If I dumped 6k, or 6 months of elbow grease with my wrenching buddy into the 400, plus 3k in parts, it still would look like a dog, with cracking paint, and I'm still not confident at that point that it's totally reliable in any circumstance.
Maybe more important is the fact that, without 10k in parts and labor to get the previous owners' "average," "non-enthusiast" maintenance caught up to where my old C was, the car will still not drive like one that has been maintained ON TIME, from DAY ONE.
The point of driving a Benz is because, in above-average condition, they will bring a smile to my face every time I drive them. The "new to me" SL is that car, and an exmaple of a car that has had EVERYTHING done on time for 19 years. The 400e really just looks and drives like a POS, except for the racehorse motor, so what joy is there in dumping money into something that isn't doing what it was designed to do, when in the case of the OP, a VERY nice 92ish 300E can be had for 3 grand.
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former: 83 300D, 97 C230, 93 400E
current: 08 C300 Luxury , 92 500SL
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