When I had a dog, she was a 55lb Chesapeake Bay Retriever. I fed her once a day.
Our black lab/shepherd mix gets fed 2x per day, a little more than a cup each time. She is trained to sit and wait but as soon as the magic word “OK!” is spoken she scarfs down everything as fast as possible.
But remember, the number of calories per cup varies considerably between brands and formulations.
A friend’s dog has intestinal problems that are controlled by feeding a high fiber, low calorie dog food. When he started the food his dog was obese. Now the dog is a normal weight but has to be fed three large meals daily to maintain his weight.
Why do you skip one? Is it to maintain dominance? And how do you make your random selection? Just curious.
The idea is to teach the dogs that we usually have meals at 8 & 8, but not always. It’s not truly random, but rather however our activities work that week. Today is Friday. If we go out to a brewery and get home after midnight, then tonight’s 8 pm feeding is skipped.
As for the random feeding concept, the keeper at a zoo who cared for the wolf display told me (and gave me some cites) that many carnivores do better when fed a certain number of calories calculated by the month but divided up randomly in a feast/famine type schedule. He fasts the animals a day or two, then feeds a large meal, then small meals, etc, with the calculated monthly calories offered being met.
You iust don’t want to be the cage cleaner on fasting day.
IMO, easier work but higher risk 
55#+ GSP (kennel dog) & 25# Parson Russell (house dog) get fed once per day, generally between 5 and 6. When I had a whole kennel full of bird dogs, and they were training/working regularly, I switched to feeding only in the evenings to a) reduce the risk of bloat, and b) make sure they were settling down and get some of that food stored, and not burn it all up while out running at top speed. It’s worked, I adjust amounts up or down depending on how much working we’re doing, and the outdoor air temps - in cold weather I feed a bit more, in warm weather I feed a bit less. It’s worked for the almost 30 years I’ve been in bird dogs.
I have a 45# Australian Shepherd, 3 years old. As a puppy, she ate twice per day, but at a certain point, she stopped eating in the morning but would eat well later in the day. I now feed her once per day, around dinner time and she eats it all and has maintained a good weight.