Judging by your list you already know what the pre
86 models are about. Take a test drive in the newer
ones and see. I hear they are smoother and faster.
Personally, I am afraid of MB automatics. I got a
new one in my 82' 300Sd and can't adjust it to my
liking. A vacuum leak is hard to pinpoint and will
cause hard shifting, if that is even my problem. I
read that their was a significant improvement to
the vac system starting in 85', but I test drove a
1986 190d that shifted poorly. Mabee the trans
was shot and would be all wonderful with a new
one, but then it might just be another vacuum problem
that a new trans will not fix. Stick to a manual.