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Personally, I think you'd be nuts to sell it at this point. The car has "high miles" in the used market, and you'd take a real kicking for the odo.
Look at it this way: (I'll use my local Canuck-bucks, but you'll get the point...)
A new E320 is about $75K.
A 2000 E320 sells for about $35K
A 1996 with 140K-miles is worth about $17K.
Suppose you buy that 2000MY car. You'll be out of pocket about $18,000. In a few years that 2000 will be an $18-20K car. That $18,000 is a sunk cost.
If you took HALF the $13K and used it as a find to keep your 1996 car going, you'd have years and years of motoring at much less cost than buying a newer car, and dramatically less than buying a brand new one. And that 2000 will require work as the warranty expires.
If the car is a money pit, maybe you should abandon ship, but it sounds solid and reliable. I would bet that you would get at least another five years and 100K-miles before any kind of major repair might be required (maybe the tranny or some minor top-end work). The bottom end of the engine will outlast practically every part of the car if you keep the oil/filter in good shape.
Some repairs you may have in the next few years:
Front suspension bushings: common W210 area.
Minor AC woes: evap temp sensor is cranky, maybe some other minor repairs.
Window regulator: another common W210 problem.
Head gasket: M104 known area of concern, but I meet many W210 M104 owners with high mileages that seem immune. Maybe the gasket problem is solved? Dare we hope?
I have bought new cars. They are poor financial decisions. They are about "I WANT it, dammit." If you're just itchy for something new and don't mind the additional moolah for the newer ride, go for it. If you're looking for the lowest per-mile option, keep your car and think about grille-badge collecting...
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