Transmission problem?
 

A few times lately when it's cold (outside temperature & car not up to full running speed), it seems like as it shifts into 2nd or 3rd gear (automatic transmission, 1983, 300 SD turbodiesel, 275,000 miles), it first spins with a higher pitched whirring sound before it 'grabs' and continues to propel the vehicle - kind of like a clutch engaging. A friend of mine riding in the car pointed this out to me recently and felt sure it was the transmission beginning to fail. Can anyone tell me if this is true, based on this limited info.? Since my friend felt so sure, then maybe someone with more mechanical knowledge and Benz experience might know? If so, can you give some estimate, however rough(!) how soon it is likely to fail, how much the repair will cost, and if there is such a thing as re-building them or does that whole part just get replaced? I have no idea what might be involved; I never had a car that required major transmission work. Thanks!

Sounds like a vac problem to me. It could have to do with your k-1,2 springs, also. Have you tried doing a search regarding shift flaring?