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Actually, the first year of the 722.6 5-speed automatic transmission was 1996 and only very early production models gave real trouble (like the new 7G transmission gave trouble with the very early production W221s).
A late production 96, a 97/98 or 99, with low miles and with proper maintenance records would be an excellent and safe choice.
Personally I prefer the S 500 over the S 320, but if you do a lot of town driving an S 320 would provide you with a slightly better MPG.
Just be sure to check all electrical systems and any fluids leaks. The smallest sign of something not working properly can mean big $$$ trouble later on.
But if everything checks out, the W140 is definitely and without a doubt the best Mercedes-Benz ride you can buy.
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A. Rosich
CL 500, 1998 
S 500 L, 1998 
E 320 T, 1995  [Sadly sold  ]
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