It could be easier...
I see Revit behaving this way, they regard the first point as ineligible to being tangent because it depends on the bearing of the line, With that assumption or bias, the first point is necessary to make a tangent condition possible. I can easily snap to a location on the pulley that couldn't be tangent to the next pulley.
AutoCAD deals with this in a clever fashion (when we invoke the tangent snap) by fixing the first point to be tangent after the second point is placed. If we aren't careful with our second pick (snap tangent too) point the tangent line might end up at the opposite side of the pulley.
In contrast, Revit handles it naively, because it regards our first point as ineligible to tangents because it isn't considering the desired end result: "I want to draw a line tangent to two circles". AutoCAD appears to know this by virtue of snapping tangent for the first point so it can adjust the final bearing of the line.
To get around this naivete, I place the first point on the pulley where it looks like it can be tangent, to my eye. The second point snaps to tangent with the icon. I return to the first point and grip/drag it away and back to let the snap icon appear, to fix it for tangent, just to see if I was close. If my guess wasn't accurate, it is now.
Steve Stafford
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