When our daughter was a toddler, we had the most difficult time getting her to treat lows- especially at night. Ages 2 and 3 are so hard! Lows are common between 1 and 3 am because they don't need as much insulin during that time of the night. Reducing the long acting insulin is what I'd start with to reduce the amount of lows. Getting him on a pump would be best to control the basal insulin better. If you get a sippy cup, take out the stopper and put his favorite sugar drink - even chocolate milk - then while he is sleeping you can put the sippy cup tip between his lips and hold onto it and pour it into his mouth that should help. Soon, he will get used to this and sleep through it. But remember they are low and confused and will do battle sometimes anyway. It's a low symptom. See if this works better. It worked for us with our toddler. She is now 6.
My other daughter got very used to me coming in her room in the night and as soon as I said the word, "Juice", she would sit straight up and drink it down and fall back asleep with no memory of the incident the next morning. He will get used to it.