Picking start pt, next pt and a preset dim offset is what you want, set next to start pt, then continue picking next point and repeat. I dont have anything that matches but its a bit like make a pline from pick pts. You would use dim align not hor or ver.
Something like this.
; https://www.cadtutor.net/forum/topic/73968-is-it-possible-to-change-dimension-orientation-while-performing-dimcontinue/
; multi dim by AlanH Nov 2021
(defun c:mdim ( / off pi2 oldsanp pt1 pt2 pt3)
(setq off 5.5 pi2 (/ pi 2.0))
(setq oldsnap (getvar 'osmode))
(setvar 'osmode 1)
(setq pt1 (getpoint "\nPick 1st point "))
(while (setq pt2 (getpoint "\nPick next point Enter to exit"))
(setq ang (angle pt1 pt2))
(setq mp (mapcar '* (mapcar '+ pt1 pt2) '(0.5 0.5 0.5)))
(setq pt3 (polar mp (+ ang pi2) off))
(setvar 'osmode 0)
(command "dim" "align" pt1 pt2 pt3 "" "exit")
(setq pt1 pt2)
(setvar 'osmode 1)
)
(setvar 'osmode oldsnap)
(princ)
)
(c:mdim)