Living on borrowed time? Maybe, Maybe not...
My 95 E300D (same basic design as your transmission) is all original with 324,000+ miles. I recently purchased the car, and was quite surprised (and a little disappointed actually) that it had never been ‘gone through’. The car had been dealer maintained its whole life, including fluid changes at MBZ recommended intervals.
That being said, almost all the mileage was accumulated by highway driving. The transmission works very well, except for one small (nit picking) problem on the 1-2 and 2-3 shifts: as it releases one gear, there is a small hesitation before the next gear engages, but it is NOT a flaring problem – it seems that it takes a fraction of a second too long for the clutch pack to fill up completely, and/or piston(s) to move. Probably an indication of the seals becoming less compliant & not holding pressure as well as they would when new. I’ll probably try to increase the modulator pressure a little bit to see if it helps…
Glenn
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Current rolling stock:
2001 E55 183,000+ Newest member of the fleet.
2002 E320 83,000 - The "cream-puff"!
1992 500E 217,000+
1995 E300D 412,000+
1998 E300D 155,000+
2001 E320 227,000+
2001 E320 Wagon, 177,000+
Prior MBZ’s:
1952 220 Cab A
1966 300SE
1971 280SE
1973 350SLC (euro)
1980 450SLC
1980 450SLC (#2)
1978 450SLC 5.0
1984 300D ~243,000 & fondly remembered
1993 500E - sorely missed. 
1975 VW Scirocco w/ slightly de-tuned Super-Vee engine - Sold after 30+ years.
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