The first year is probably the worst because not only are you trying to learn the rules of the game, you've also got the honeymoon period kicking in so that while you're trying to figure out the right amount of insulin for a certain amount of food, your pancreas then decides it's had a bit of a rest and starts squirting out insulin to throw your calcs out.
But that will pass. Hypos are never pleasant, they will still happen no matter how careful we are, but if it's any small comfort to a parent, they're not painful and the worst which will usually happen is that we come round thinking that wasn't much fun. I've found that when I try something new, a job, hobby, sport, whatever, I usually learn more from the mistakes than from getting it right. Your boy has now learned that exercise lowers blood sugar, so that while he might take X units for a meal one day, he should take a smaller amount the next day if he's going swimming. There's no easy answers to all of this, but all of us usually reach a point where we're sitting down to have a meal and we'll say, ok, based on what's happened in the last day and what I expect to do in the next few hours, I reckon X units will cover it. Takes a while to figure out the variables, and I sure as hell still make a lot of mistakes even after 28 years, but it's totally do-able. Embrace the mistakes as a learning experience!