TL;DR
How do you calibrate this thing in JMRI?
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So I have come to the conclusion that do to "reasons" (jhidrawplugin-win.dll only existing in 32bit form) Raildriver only works on 32bit versions of JMRI. This Translates to using version 4.26 as the last 32bit compatible version.
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So after downgrading I do actually get the "raildriver" menu item (under debug) to do something. I does actually seem like it's trying to work, unfortunately it is said that one should calibrate the deadzones least it overloads JMRI and it runs out of memory.
Well that seems to be exactly what is happening.
Where is this calibration window that never seems to appear?