You may want to consider using a synthetic ATF this time around. It did wonders for my 1982 300D that was experiencing a 3-4 shifting problem when cold. Since changing to synthetic the problem cleared immediately. I think the synth has better cleaning properties and is probably a little slicker and flows better, especially at cold temperatures.

The only thing I could find locally was Quaker State 4x4 Synthetic, which seems to be good. I understand Mobile has a synthetic ATF but I have not found it around here yet.

To me, not shifting properly could easily be a dirt / varnish / crud buildup in the valve body that a good fluid can help clean out.

Transmission fluid change maintenance seems to be very critical for the vintage MBs.

Also, what I do for the torque convertor drain is turn the engine (clockwise only viewed from the front) enough to get close, and then use a large screwdriver to gently coax the drain into position. Almost impossible to get it into position by just turning over the engine.

Ken300D

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1982 300D at 351K miles
1984 300SD at 217K miles
1987 300D at 370K miles