Followup....

You can't do both ends directly in the UI. However using Lisp, you can get both but it's a 2 step operation.

(setq Item_Number 1)
(setq Item_Size 2)
(setq Item_Elevation 3)
(setq Item_Alias 4)
(setq Item_Set 5)
(setq Item_Length 6)
(setq Item_Custom 7)

(defun c:addalltxt()
  (setq textSize (getvar "TextSize"))
  (setq textSize (+ textSize (/ textSize 10)))

  (setq obj (entsel))
  (setq ent (car obj))
  (setq pnt (cadr obj))

;;;  (AddTextAtPoint Item_Number ent pnt)
;;;  (setq pnt (list (car pnt) (+ (cadr pnt) TextSize) (caddr pnt)))

  (AddTextAtPoint Item_Size ent pnt)
  (setq pnt (list (car pnt) (+ (cadr pnt) TextSize) (caddr pnt)))

;;;  (AddTextAtPoint Item_Elevation ent pnt)
;;;  (setq pnt (list (car pnt) (+ (cadr pnt) TextSize TextSize TextSize) (caddr pnt)))
;;;
;;;  (AddTextAtPoint Item_Alias ent pnt)
;;;  (setq pnt (list (car pnt) (+ (cadr pnt) TextSize) (caddr pnt)))
;;;
;;;  (AddTextAtPoint Item_Set ent pnt)
;;;  (setq pnt (list (car pnt) (+ (cadr pnt) TextSize) (caddr pnt)))
;;;
;;;  (AddTextAtPoint Item_Length ent pnt)
;;;  (setq pnt (list (car pnt) (+ (cadr pnt) TextSize) (caddr pnt)))
;;;
;;;  (AddTextAtPoint Item_Custom ent pnt "Spool")
;;;  (setq pnt (list (car pnt) (+ (cadr pnt) TextSize) (caddr pnt)))

  (princ)
)

The Lisp came from here and I've commented out the sections for other annotation types...

http://www.xtracad.com/forum/index.php?topic=13151.0

Shoutout to Josh Merchant/Midlands Mechanical, the author.

Run the Lisp to tag one end. Then Hold the TAB key while you run the Lisp to tag the other end.