In a 6 quart stock pot, fill ⅔ with water and set to boil on high.
Quarter the red potatoes and cut any larger potatoes so that the pieces are all about the same size (a little larger than bite size). Set aside.
When water is boiling, add ¼ Cup of Kosher salt to the water and then add the potatoes to the water very carefully. Boil potatoes until a fork can pierce the potato easily. Drain into a colander in the sink. Allow to sit until room temperature and then place into a large bowl.
Using a potato masher, mash the potatoes gently until most are about bite size pieces. It is ok if some are larger and some much smaller. When you are satisfied with the consistency of the potatoes, begin to add the other ingredients.
Add Olive oil, vinegar, mayo, sour cream, pepper, bacon pieces, green onions, cheese, cayenne and sugar all at once. Then, using a large spatula or spoon begin to gently mix until everything is mixed throughout.
Cover the bowl with plastic wrap or aluminum foil and place into the refrigerator overnight or at least for a few hours to allow the flavors to meld.
Serve Cold