@Kent1Cooper wrote:
.... Offset, use a Lengthen command with the Delta option and the negative of the Offset distance to shorten the ends of the result of Offsetting, and then put in arrows from the start of the original to the start of the new, and similarly between the ends of each. What should the arrows be? Leaders? ....
This is the idea described above, assuming Leaders as the answer to that question. In simplest terms, lightly tested:
(defun C:OAL (/ ent1 ent2); = Offset with Angled Leaders
(command
"_.offset" pause (setq ent1 (car (entsel))) pause ""
"_.lengthen" "_delta" (- (getvar 'offsetdist))
(vlax-curve-getStartPoint (setq ent2 (entlast)))
(vlax-curve-getEndPoint ent2)
""
"_.chprop" ent2 "" "_layer" (getvar 'clayer) ""
"_.leader"
(vlax-curve-getStartPoint ent1)
(vlax-curve-getStartPoint ent2) "" "" "_none"
"_.leader"
(vlax-curve-getEndPoint ent1)
(vlax-curve-getEndPoint ent2) "" "" "_none"
); command
(princ)
); defun
It even works on Arcs, or Polylines with arc segments at their ends, or Splines, though the angle of the Leader will be slightly off, varying with the tightness of the curve.

BUT NOTE several things:
It's based on your original image. It requires a single object, so it won't do the inboard part of the left side of your image in Message 6 [I'm having a hard time imagining how to do that in a way that a routine could figure out], and in the right side, it would require the two inside edges of each L, and only those two edges, to be joined together into a Polyline.
It assumes the Erase option in Offset is set to No -- that could be built into it just in case.
It only shortens the ends of the Offset result. Presumably it might be made to check the length of the selected object and/or of the result from Offsetting, and if it's too short to shorten both ends by the Offset distance, make them longer instead, like the top-end parts of the left half of your image in Message 6.
It requires the current Dimension Style's arrowhead for Leaders to be a suitable type [presumably some kind of arrow but not the Right-angle variety, rather than, for example, a tick or datum triangle or ...], and appropriately sized for the Offset distance. Presumably it could be made to either set the Offset distance itself based on the current arrow size, rather than ask the User, or alter the arrow size based on the User's specified Offset distance.
The angled Leaders at the ends are separate from the Offset object connecting them [which is, of course, a Line or Polyline or Arc or Spline or...]. One advantage of having it make a Polyline with width variations making the arrowheads, rather than using Leaders, would be that the whole thing would be one object, but that would limit the object types it could work on [no Splines, for instance].
It could be made to offer a choice of angles, but when you say you want a 30-degree option, which 30 degrees do you mean?

Kent Cooper, AIA