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Shrinkwrap constraint is pretty good for this, to control how far your object is from the ground you can simply lift it in edit mode to move it's origin downward.


Here are 2 pistons one with with 2 and one with 3 sections I got the solution from Here after using the track to constraint instead of the damped track which I mistakenly took for a look at constraint from 3ds max. The Track to constraint has all sorts of issues like spinning mesh the Damped track doesn't seem to. I realize after 7 months you probably ...

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