I really doubt anybody will read through this whole thing, but if so:

I tried disconnecting the vacuum hose to the tranny and took it for a spin. The shifts seemed a little more sloppy/slappy/harsh. It WOULD downshift into third when I told it to, i.e. coasting and dropping the lever. But it would NOT downshift into second unless I pushed on the old pedal.

Regardless of whether the hose was connected or not, If I start out in 2, it will not up shift into 2 until I throw it into 3. If I immediately downshift back into 2, it will stay in 2. I don't know if this is related at all, but it's info.

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B
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1983 300SD