How can get the red auto-measurements between objects to activate always? I don’t see the rhyme or reason for when it shows and when it disappears. I would love to see it all the time.
Thanks 
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Press Alt/Option to see distances between the selected and hovered object.
Yes, the hover+Option trick. What I’m talking about is when the measurements magically appear on their own as I’m situating an object. There seems to be no rhyme or reason as to when it decides to magically appear and when it decides to magically disappear. Is there a setting to switch on?
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Oh, you mean snapping lines. They are smart guides that appear when you are moving an object to the distance that is similar to the distance between other objects. For example you have two rectangles in a row with 20px spacing between, and when you move the third object to 20px from the second rectangle, the measurement line will be shown and the object will snap to this measurement. There is no way to make them appear at all times.
So, are they sentient and decide on their own when they want to come out and play and when they don’t want to come out and play?
Is there any logic? If so, what is it?
Is this a bug that’s currently being fixed?
There is no way to make them appear at all times as that’s not their intended purpose. They appear like I described — when the distances between close objects are the same. This is the logic. Here is an example:
Vote for this suggestion: Showing distance to objects while dragging