gistfile1.el

(defun my/fix-space ()
  "Delete all spaces and tabs around point, leaving one space except at the beginning of a line."
  (interactive)
  (just-one-space)
  (when (looking-back "^[[:space:]]+") (delete-horizontal-space)))
  
(defun my/delete-backward ()
  "When there is an active region, delete it and then fix up the whitespace."
  (interactive)
  (when (use-region-p)
    (delete-region (region-beginning) (region-end))
    (my/fix-space)))  

;; Same as above, but using (interactive "r") to get the bounds of the region    
(defun my/delete-backward-2 (beg end)
  (interactive "r")
  (when (use-region-p)
    (delete-region beg end)
    (my/fix-space)))

;;    
;; Variant that deletes backward one char unless the region is active:
;;

(defun my/delete-backward ()
  (interactive)
  (if (use-region-p)                  ; IF

    (progn                            ; THEN
      (delete-region (region-beginning) (region-end))
      (my/fix-space))

    (delete-backward-char 1)))        ; ELSE
    
;;
;; Improved version of the last example that handles a prefix arg the same way as `delete-backward-char.
;; - If there is no region: delete backward one character, or N characters with a prefix argument.
;; - If the region is active and the prefix arugment is 1 (or not set), delete the region and fix space.
;; - If the region is active you can use a prefix arg to delete a certain number of chars instead of the region.

(defun my/delete-backward (n)
  (interactive "p")
  (if (and (use-region-p) (= n 1))
      (progn
        (delete-region (region-beginning) (region-end))
        (my/fix-space))
      (delete-backward-char n)))

Related discussion on Emacs StackExchange:
http://chat.stackexchange.com/rooms/23774/discussion-between-glucas-and-peter-salazar

The chatroom is gone, so I'll just comment here. First, thank you so much! This is so incredibly helpful. Really appreciate you taking the time to do that.

The custom functions you created above addresses most everything I would ever encounter. I discovered only a few cases that don't behave as expected. In each case below, I'm highlighting the words called "delete" and then hitting the delete key on my MacBook. In the second and third case, I'm also highlighting the comma and space that come before. In each case, I wind up with an extra space before the end of the sentence.

Lorem ipsum delete delete delete, consectetur adipiscing elit.  

Lorem ipsum dolor, delete delete delete.  

Lorem ipsum dolor, delete delete delete?  

I think this should do it:

(defun my/fix-space ()
"Delete all spaces and tabs around point, leaving one space except at the beginning of a line and before a punctuation mark."
(interactive)
(just-one-space)
(when (or (looking-back "^[[:space:]]+")
(looking-at "[[:punct:]]"))
(delete-horizontal-space)))