This does sound like the issue with the car.

Since I'm going to be messing with the transmission is there any other recommended maintenance/part-replacement that I can do at the same time?

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JWJ
1983 MB 300D - > 430,000 miles - Deep Blue - Bilstein Comforts - 0-60 in 24 seconds - 27MPG
1985 MB 300TD (wagon) - > 275,000 miles - Manila Beige - Thule rack - 0-60 in 18 seconds - 22 - 25MPG
Biodiesel, Mobil Delvac 1, and Viton fuel lines!