Hi, love the pics. He's very cute. How old is Iggy? I don't think you're over feeding him, I fed my two guys 1 cup three times a day while they were small puppies, they ate at 8 am, 2pm, and again at 8 pm, so it's almost the same schedule as yours. We switched them to 2 feedings a day when they were 7 months old. What time do you take him out in the morning? Is it when you wake up, or do you set the alarm clock? What we did was we would set the alarm clock for 6 am and take them out , then did the every hour or two schedule throughout the day, with the last outing at about 11 or 11:30 pm, then we would set our cell phone alarm for 2 am, to go out, as the time between 11 pm at night to 6am is too long a time for a puppy to hold, we did this until they were 5 months old, and then were able to eliminate the middle of the night outing, but we still set the morning alarm for 6 am before they can go in the crate. Good luck.